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Acetonitrile → 1-(2-Chloro-5-thiazolylmethyl)-3,3-dimethyl-2-nitro-1-phenoxythiocarbonylguanidine

HRID 1657037
Notes
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Reaction equation

HRID 1657037 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][NH:8][C:9]([N:14]([CH3:16])[CH3:15])=[N:10][N+:11]([O-:13])=[O:12])=[CH:5][N:6]=1.C([O-])([O-])=O.[K+].[K+].CC#N.[CH:26]1[CH:31]=[CH:30][C:29]([O:32][C:33](Cl)=[S:34])=[CH:28][CH:27]=1>O>[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]([C:33]([O:32][C:29]2[CH:30]=[CH:31][CH:26]=[CH:27][CH:28]=2)=[S:34])[C:9]([N:14]([CH3:16])[CH3:15])=[N:10][N+:11]([O-:13])=[O:12])=[CH:5][N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 70498Phenyl thioxochloroformateHCID 136218199N-(2-chloro-5-thiazolylmethyl)-N',N'-dimethyl-N"-nitroguanidine

Product 1

HCID 538143491-(2-Chloro-5-thiazolylmethyl)-3,3-dimethyl-2-nitro-1-phenoxythiocarbonylguanidineYield 75.8%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Procedure

To a mixture of 1-(2-chloro-5-thiazolylmethyl)-3,3-dimethyl-2-nitroguanidine (200 mg), K2CO3 (420 mg) and CH3CN (13 ml) was added phenyl chlorothionoformate (260 mg) dropwise in 3 minutes at 3° C. under stirring. After stirring at room temperature for 4 hours, water (10 ml) was added to the mixture which was extracted with CHCl3 (20 ml). The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was crystallized from AcOEt-Et2O to afford 230 mg of 1-(2-chloro-5-thiazolylmethyl)-3,3-dimethyl-2-nitro-1-phenoxythiocarbonylguanidine (Compound No. 44) as a white crystal, m.p. 161°-162° C.

Workup

  1. stirringAfter stirring at room temperature for 4 hours
  2. extractionwas extracted with CHCl3 (20 ml)
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was crystallized from AcOEt-Et2O

Sources & evidence

ORD record
ord-fba465e79bf647b3bec8433209485ee8
Source dataset
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05256679

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes