Thiophosgene → HCID 19438780, compound

HRID 1733893Notes

Reaction equation

HRID 1733893 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH2:5]([O:12][N:13]1[C:22]2[C:17](=[CH:18][C:19]([N:27]3[CH:31]=[CH:30][N:29]=[CH:28]3)=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=2)[N:16]=[C:15]([NH:32][NH2:33])[C:14]1=[O:34])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O1CCCC1.CN(C)C=O>[CH2:5]([O:12][N:13]1[C:22]2[C:17](=[CH:18][C:19]([N:27]3[CH:31]=[CH:30][N:29]=[CH:28]3)=[C:20]([C:23]([F:24])([F:25])[F:26])[CH:21]=2)[N:16]2[C:1](=[S:2])[NH:33][N:32]=[C:15]2[C:14]1=[O:34])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 19438751HCID 19438751, compound

Product 1

HCID 19438780HCID 19438780, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of thiophosgene (1.1 ml, 14 mmol) in 10 ml of dry tetrahydrofuran was added dropwise to a stirred solution of 2.91 g (7 mmol) of 1-benzyloxy-3-hydrazino-6-(1H-imidazol-1-yl)-7-trifluoromethylquinoxalin-2(1H)-one in a mixture of 100 ml of dry tetrahydrofuran and 25 ml of dry N,N-dimethylformamide at 0° C. The mixture was stirred for 2h at 0° C. and evaporated to dryness. The solid residue was suspended in 100 ml of water, neutralized with solid sodium hydrogen carbonate and filtered. Recrystallization from ethanol afforded 1.64 g (51%) of the title compound.

Workup

  1. customevaporated to dryness
  2. filtrationfiltered
  3. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-be6156e0ac8f4063b90735bf4f0542e5
Source dataset
uspto-grants-1996_07
Patent number
US05532236

Reaction notes

Loading…