Dimethylformamide → HCID 54433057, compound

HRID 617076Notes

Reaction equation

HRID 617076 reaction equation
[C:1]1([C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][N:9]=[C:10]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[C:11]([O-])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([NH+](CC)CC)C.C(Cl)(=O)C([Cl:41])=O.CN(C)C=O>C(Cl)Cl>[C:1]1([C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][N:9]=[C:10]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[C:11]([Cl:41])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86734466HCID 86734466, compound

Product 1

HCID 54433057HCID 54433057, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of triethylammonium 2-triphenylmethoxyimino-2-(thien-2-yl)-acetate (syn isomer) (2.30 g, 4.46 mmole) in dry methylene chloride (50 ml) was cooled to 0° to +5° and stirred whilst oxalyl chloride (0.38 ml, 4.46 mmole) was added. N,N-Dimethylformamide (ca 0.1 ml) was added and the mixture was stirred at 0° to +5° for 21/2 hours. The solvent was evaporated and the residue was stirred with ether (100 ml) for 1 hour, and the suspension then filtered. The filtrate and ether washings (100 ml) were evaporated to give the title compound as a white crystalline solid (1.985 g, quantitative). This acid chloride was used without further purification.

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. stirringthe residue was stirred with ether (100 ml) for 1 hour
  4. filtrationthe suspension then filtered
  5. customThe filtrate and ether washings (100 ml) were evaporated

Sources & evidence

ORD record
ord-53a32d10698244739e2026fb514b8a94
Source dataset
uspto-grants-1978_02
Patent number
US04076936

Reaction notes

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