Iodoacetamide → 2-((2-Methylbenzoyl)imino)-5-nitro-3(2H)-thiazoleacetamide

HRID 1701836Notes

Reaction equation

HRID 1701836 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:20]=[CH:19][CH:18]=[CH:17][C:5]=1[C:6]([NH:8][C:9]1[S:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][N:13]=1)=[O:7].[H][H].I[CH2:24][C:25]([NH2:27])=[O:26]>CN(C)C=O>[CH3:3][C:4]1[CH:20]=[CH:19][CH:18]=[CH:17][C:5]=1[C:6]([N:8]=[C:9]1[N:13]([CH2:24][C:25]([NH2:27])=[O:26])[CH:12]=[C:11]([N+:14]([O-:16])=[O:15])[S:10]1)=[O:7]

Participants

6

Reactant 4

HCID 3727IodoacetamideHCID 24758Sodium hydrideHCID 3113444HCID 3113444, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 30618262-((2-Methylbenzoyl)imino)-5-nitro-3(2H)-thiazoleacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride in mineral oil (2.1 g, 60% w/w) was added in portions to a stirred suspension of 2-methyl-N-(5-nitro-2-thiazolyl)benzamide (10.5 g) in N,N-dimethylformamide (100 ml). When the evolution of hydrogen ceased, 2-iodoacetamide (11.1 g) was added in portions. The mixture was stirred at room temperature for ca 1 hr., then poured into ice-water. Recrystallization of the separated solid from acetic acid afforded 2-[(2-methylbenzoyl)imino]-5-nitro-4-thiazoline-3-acetamide, m.pt 248°-250°.

Workup

  1. customRecrystallization of the separated solid from acetic acid

Sources & evidence

ORD record
ord-0725cc077b954afd880f537e7a41bdf6
Source dataset
uspto-grants-1983_04
Patent number
US04379156

Reaction notes

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