Benzoyl chloride → HCID 14435469, compound

HRID 1585215Notes

Reaction equation

[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[C:22]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: -25 °C

Procedure

In 400 ml of tetrahydrofuran, 42.0 g of 3-phenyl indole was solved. The solution and 25.0 g of potassium tert-butoxide added thereto at -30--20° C. were together heated to normal room temperature and stirred for 30 minutes. The reaction solution was cooled to -20--10° C. and 26 ml of benzoyl chloride added thereto were together heated to normal room temperature and stirred for one hour. The resultant mixture was poured into ice water and extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate, distilled to expel the chloroform, crystallized by addition of isopropyl ether, separated by filtration, and dried to obtain 60.0 g of 1-benzoyl-3-phenylindole (92.8%) having a melting point of 154-156° C.

Workup

temperatureThe reaction solution was cooled to -20--10° C.
temperaturethereto were together heated to normal room temperature
stirringstirred for one hour
extractionextracted with chloroform
dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
distillationdistilled
customcrystallized by addition of isopropyl ether
customseparated by filtration
customdried

Sources & evidence

ORD record: ord-82121b6e81094b6e895e9bf985be0c44
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05936098

Reaction notes

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