Benzyl mercaptan → HCID 22123564, compound

HRID 362439Notes

Reaction equation

[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[CH:26][C:17]=1[C:18]([C:20]1[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=1)=[O:19]>CN(C)C=O>[CH2:1]([S:8][C:16]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[CH:26][C:17]=1[C:18]([C:20]1[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=1)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Benzylmercaptan (4.3 g) and potassium carbonate (4.8 g) were added to a solution of 2-(2'-chloro-3'-nitro-benzoyl)-1-methyl-imidazole (9.2 g) in 150 ml of N,N-dimethyl-formamide. The reaction mixture was stirred at 80° C. for 5 hours. Then, the reaction mixture was poured onto ice water, and the resulting mixture was extracted twice with ethyl acetate. The combined organic phases were washed with water and then dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure and the remaining residue was purified by silica gel column chromatography (eluting solvent:hexane/ethyl acetate=95:5 v/v). 2-(2'-Benzylthio-3'-nitro-benzoyl)-1-methylimidazole (8.7 g) was obtained in this manner.

Workup

additionThen, the reaction mixture was poured onto ice water
extractionthe resulting mixture was extracted twice with ethyl acetate
washThe combined organic phases were washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationThe organic phase was concentrated under reduced pressure
customthe remaining residue was purified by silica gel column chromatography (eluting solvent:hexane/ethyl acetate=95:5 v/v)

Sources & evidence

ORD record: ord-fa08e9555e7047d5aeaf4692f3808472
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869508

Reaction notes

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