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Water → 3-(4-Trifluoromethylphenyl)-2-propenyl(s)-4-{3-[2-(2-chloro-6-nitrophenylthio)-4-nitroimidazol-1-yl]-2-hydroxy-2-methylpropyl}piperazin-1-carboxylate

HRID 1158291
Notes
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Reaction equation

HRID 1158291 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[S:16][C:17]1[N:18]([CH2:25][C@:26]2([CH3:29])[CH2:28][O:27]2)[CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[N:21]=1.[N:30]1([C:36]([O:38][CH2:39][CH:40]=[CH:41][C:42]2[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][CH:43]=2)=[O:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.O>C(OCC)(=O)C>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[S:16][C:17]1[N:18]([CH2:25][C@:26]([OH:27])([CH3:29])[CH2:28][N:33]2[CH2:32][CH2:31][N:30]([C:36]([O:38][CH2:39][CH:40]=[CH:41][C:42]3[CH:47]=[CH:46][C:45]([C:48]([F:50])([F:51])[F:49])=[CH:44][CH:43]=3)=[O:37])[CH2:35][CH2:34]2)[CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[N:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 665893003-(4-Trifluoromethylphenyl)-2-propenyl piperazine-1-carboxylateHCID 86604374(R)-2-(2-chloro-6-nitrophenylthio)-1-(2-methyl-2-oxiranylmethyl)-4-nitroimidazole

Product 1

HCID 86604373
3-(4-Trifluoromethylphenyl)-2-propenyl(s)-4-{3-[2-(2-chloro-6-nitrophenylthio)-4-nitroimidazol-1-yl]-2-hydroxy-2-methylpropyl}piperazin-1-carboxylate
Yield 89.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N,N-Dimethylformamide (0.25 ml) solution of (R)-2-(2-chloro-6-nitrophenylthio)-1-(2-methyl-2-oxiranylmethyl)-4-nitroimidazole (55 mg) and 3-(4-trifluoromethylphenyl)-2-propenyl piperazin-1-carboxylate (51 mg) was stirred at 60° C. for 1 day. To the reaction mixture was added water and ethyl acetate, the organic layer was taken by separation. The ethyl acetate layer was washed with water and an aqueous solution being saturated with sodium chloride, then dried over anhydrous sodium sulfate. The residue obtained by removal of the solvent by distillation was purified by use of a thin layer chromatography (eluent: dichloromethane/methanol=30/1), there was obtained 3-(4-trifluoromethylphenyl)-2-propenyl(S)-4-{3-[2-(2-chloro-6-nitrophenylthio)-4-nitroimidazol-1-yl]-2-hydroxy-2-methylpropyl}piperazin-1-carboxylate (91 mg, yield: 87%) as yellow amorphous product.

Workup

  1. customthe organic layer was taken by separation
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by removal of the solvent by distillation
  5. customwas purified by use of a thin layer chromatography (eluent: dichloromethane/methanol=30/1)

Sources & evidence

ORD record
ord-65bbbee79de443f0a7a402e469b37615
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07807843B2

Reaction notes

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