Acetic Anhydride → HCID 21424975, compound

HRID 258882Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH:8]=[C:7]([C:16]#[C:17][CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][OH:27])[CH2:21][CH2:20]3)[C:6]=2[CH:28]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>>[C:29]([O:27][CH2:26][CH2:25][N:22]1[CH2:21][CH2:20][N:19]([CH2:18][C:17]#[C:16][C:7]2[C:6]3[CH:28]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH:8]=2)[CH2:24][CH2:23]1)(=[O:31])[CH3:30]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 21424935HCID 21424935, compound

Product 1

HCID 21424975HCID 21424975, compound

Procedure

A solution of 5.0 g. of 2-{4-[3-(8-chloro-dibenzo[b,f]thiepin-10-yl)-2-propynyl]-1-piperazinyl}-ethanol in 50 ml. of acetic anhydride is heated for 15 minutes on a steam-bath. After evaporation of the excess acetic anhydride under greatly reduced pressure, the resulting oil is taken up in ether and washed with saturated sodium bicarbonate solution. By concentration of the ethereal phase, there is obtained 2-{4-[3-(8-chloro-dibenzo[b,f]thiepin-10-yl)-2-propynyl]-1-piperazinyl}-ethyl acetate which melts at 96°-99° C. after recrystallization from ethyl acetate/hexane.

Workup

customAfter evaporation of the excess acetic anhydride under greatly reduced pressure
washwashed with saturated sodium bicarbonate solution

Sources & evidence

ORD record: ord-358342e700a64a2a9b9e472a629e511f
Source dataset: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04035386

Reaction notes

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