KRS_040_001 (Experiment #59)

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Synthesis of N-(4-methylpyridin-2-yl)-4-(p-tolyl)-thiazol-2-amine

Link to HIRAC

Reaction Scheme

Reaction Table

Reagents	KRS_033	KRS_026	EtOH
Equivalents	1	1	-
Molecular weight (g/mol)	213.07	167.23	-
Mass (grams)	0.118	0.094	-
Number of moles (mmol)	0.554	0.554	-
Volume (mL)	-	-	2.5

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Procedure

1. KRS_035 dissolved in EtOH.
2. Addition of KRS_026.
3. Heated to reflux (78 °C), clear solution with a precipitate forming within minutes (11:16)

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4. TLC at 13:45 with 10% EtOAc in petroleum benzine and KMnO₄ indicated complete consumption of KRS_026 (didn't have any a-bromoketone - used all in the reaction, whoops!)

   

5. Reaction cooled to room temperature and left stirring until 15:40.

6. Poured over ice water (~10 mL)

7. pH adjusted to ~ 10 with a saturated aqueous solution of Na2CO3 (starting pH was 3) to precipitate the product. A very pale yellow solid formed

8. The precipitate was collected via vacuum filtration and washed with ice water (2 x 10 mL) followed by cold hexane (2 x 10 mL) and dried under vacuum for 5 minutes.

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9. ¹H NMR indicated product

NMR Raw Data KRS_040_001_1.zip

Yield

Product is a pale yellow solid Experimental: 127 mg Theoretical: 156 mg Percentage: 82%

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Raw and processed IR, NMR (¹H, ¹³C, COSY, HSQC and HMBC) and HRMS