Acetic Anhydride → HCID 13060845, compound

HRID 2286274Notes

Reaction equation

HRID 2286274 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([SH:13])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[CH:14]1[C:19]([C:20]([CH2:22][Br:23])=O)=[CH:18][CH:17]=[C:16](Cl)[CH:15]=1.C(=S)([S-])N.[NH4+].Br[CH:31](C1C=CC=CC=1)[C:32]([OH:34])=[O:33].C(OC(=O)C)(=O)C>C(O)(=O)C.CC(C)=O>[Br-:23].[C:32]([O:34][C:22]1[N+:9]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[CH:12][S:11][C:10]=2[S:13][C:20]=1[C:19]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:33])[CH3:31]

Participants

8

Reactant 5

HCID 7918Acetic AnhydrideHCID 68303p-Chlorophenacyl bromideHCID 97919Bromo(phenyl)acetic acidHCID 11083854Ammonium dithiocarbamateHCID 178527837HCID 178527837, compound

Product 1

HCID 13060845HCID 13060845, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent

Procedure

A mixture of 10.0 g. (0.044 m.) 4-(4-chlorophenyl)-2-mercaptothiazole (prepared by the reaction of α-bromo-4-chloroacetophenone with ammonium dithiocarbamate) and 10.0 g. (0.04 m.) α-bromophenylacetic acid in 200 ml. of acetone and 40 ml. each of glacial acetic acid and acetic anhydride is heated for 2 hours. After the solvents are removed, the residual solid is triturated with acetone and the resulting solid collected. 10 g. (58% yield) of the title product is obtained, m.p. 160°-165° C.

Workup

  1. additionA mixture of 10.0 g
  2. customAfter the solvents are removed
  3. customthe residual solid is triturated with acetone
  4. customthe resulting solid collected

Sources & evidence

ORD record
ord-5875f1818272432c94a097031811a804
Source dataset
uspto-grants-1982_04
Patent number
US04327221

Reaction notes

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