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Triethylamine → 2-(4-Phenoxythiocarbonylthiophenyl)-3-(4-pyridyl)-6,7dihydro[5H]-pyrrolo[1,2-a]imidazole

HRID 1885598
Notes
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Reaction equation

HRID 1885598 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH2:21][CH2:20][CH2:19][N:11]3[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:29]1[CH:34]=[CH:33][C:32]([O:35][C:36](Cl)=[S:37])=[CH:31][CH:30]=1>COCCOCCOC>[O:35]([C:36]([S:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH2:21][CH2:20][CH2:19][N:11]3[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1)=[S:37])[C:32]1[CH:33]=[CH:34][CH:29]=[CH:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70498Phenyl thioxochloroformateHCID 135962046(4-mercaptophenyl) 3 (4-pyridyl) 6,7dihydro[5H]-pyrrolo[1,2-a]imidazole

Product 1

HCID 198792422-(4-Phenoxythiocarbonylthiophenyl)-3-(4-pyridyl)-6,7dihydro[5H]-pyrrolo[1,2-a]imidazole

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

To an ice bath cooled solution containing 1.0 g (3.4 mmole) of 2-(4-mercaptophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole prepared as in Example 16 and 0.5 ml (3.6 mmole) of triethylamine in 10 ml of diglyme is added 0.48 ml (3.5mmole) of phenyl chlorothionoformate. The reaction is allowed to warm to room temperature and heated at 40° to 120° C. for several hours. Workup and chromatography in a manner analogous to that outlined in Example 18 affords the desired titled compound.

Workup

  1. temperatureTo an ice bath cooled solution
  2. additioncontaining
  3. temperatureheated at 40° to 120° C. for several hours

Sources & evidence

ORD record
ord-5986c07526c44026acc3095e31932735
Source dataset
uspto-grants-1992_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05145858

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes