Triethylamine → 7-(4-Chlorobenzoyl)-3-methylthioindolin-2-one

HRID 1704321Notes

Reaction equation

[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5].ClOC(C)(C)C.[CH3:23][S:24][CH2:25][C:26](OCC)=[O:27].C(N(CC)CC)C>C(Cl)Cl>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]([C:3]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:2]=2[NH:1][C:26](=[O:27])[CH:25]3[S:24][CH3:23])=[O:5])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: -65 °C

Procedure

A solution of 23.1 g. (0.1 mole) of 2-amino-4'-chlorobenzophenone in 400 ml. of methylene chloride was cooled to -65° C. and treated dropwise with 12.4 g. (0.1 mole) of t-butyl hypochlorite. After 15 min., 13.4 g. of ethyl α-(methylthio)acetate (0.1 mole) was added dropwise maintaining -65° C. temperature. After 11/2 hr. 10.1 g. of triethylamine (0.1 mole) was added and the reaction mixture allowed to come to room temperature. The solution was then washed with water and stripped. The residue was taken into methanol and brought to reflux at which time 1N hydrochloric acid was added and the resulting mixture refluxed overnight. The mixture was cooled, resulting precipitate filtered off and recrystallized from toluene, giving 10 g. of a cream colored solid. The product (33% yield) melted at 186°-188° C.

Workup

additiontreated dropwise with 12.4 g
custom2 hr
customto come to room temperature
washThe solution was then washed with water
temperatureto reflux at which time 1N hydrochloric acid
additionwas added
temperaturethe resulting mixture refluxed overnight
temperatureThe mixture was cooled
customresulting precipitate
filtrationfiltered off
customrecrystallized from toluene
customgiving 10 g

Sources & evidence

ORD record: ord-3e5f0656394944539d204fd02a31be54
Source dataset: uspto-grants-1978_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04126635

Reaction notes

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