Diiodomethane → HCID 58016070, compound

HRID 1776151Notes

Reaction equation

HRID 1776151 reaction equation
N[C:2]1[S:3][C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.C(I)[I:19]>CC#N>[I:19][C:2]1[S:3][C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1

Participants

4

Reactant 2

HCID 6346DiiodomethaneHCID 73239Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate

Product 1

HCID 58016070HCID 58016070, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate (6.1 g, 25 mmol), prepared according to known procedure (Yamaguchi K. et al. Biorg. Med. Chem. Lett. 1999, 9(7), 957-960), was dissolved in MeCN (240 ml) and treated with CH2I2 (7 ml, 150 mmol) isoamylnitrite (12 ml, 112.5 mmol). The reaction was stirred at room temperature for 1 hour. The solvents were removed under high vacuum and the mixture was submitted to flash chromatography by eluting with light petroleum/ethyl acetate (9:1) to give the title compound as a solid. Yield: 57%.

Workup

  1. customThe solvents were removed under high vacuum
  2. washby eluting with light petroleum/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-acfe0fb876174091becb7032f670973d
Source dataset
uspto-grants-2016_02
Patent number
US09265769B2

Reaction notes

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