Water → HCID 54012179, compound

HRID 1417478Notes

Reaction equation

C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[CH2:12]([N:19]1[C:31]2[C:30]([S:32][CH3:33])=[C:29]([CH2:34][C:35]([NH2:37])=O)[CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>N1C=CC=CC=1>[CH2:12]([N:19]1[C:31]2[C:30]([S:32][CH3:33])=[C:29]([CH2:34][C:35]#[N:37])[CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

32 mg of p-toluene sulfonyl chloride was added to a solution of 20 mg of 9-benzyl-1-methylthiocarbazole-2-acetamide, as obtained in Example 75, in 0.6 ml of pyridine at room temperature. The reaction mixture was then heated to 60° C. and stirred for 2 hours. The reaction mixture was then cooled to room temperature and water was added. The aqueous layer was extracted with ethyl acetate, and the organic extract was washed with a 0.5N aqueous solution of hydrochloric acid, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 50 mg of silica gel using, as eluent, a 4:1 by volume mixture of hexane and ethyl acetate to yield 18 mg of the title compound as an oil.

Workup

temperatureThe reaction mixture was then cooled to room temperature
extractionThe aqueous layer was extracted with ethyl acetate
extractionthe organic extract
washwas washed with a 0.5N aqueous solution of hydrochloric acid
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated by evaporation under reduced pressure
additionas eluent, a 4:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record: ord-6279b3680e10489281ef5cc9f1e8295c
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05877199

Reaction notes

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