Acetic Acid → rac-[(5-Chloro-1,3-benzothiazol-2-yl)thio](phenyl)acetic Acid

HRID 64629

Reaction equation

HRID 64629 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([SH:10])=[N:7][C:6]=2[CH:11]=1.Br[CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]([OH:16])=[O:15].CC(C)=O.C(O)(=O)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]([OH:16])=[O:15])=[N:7][C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 97919Bromo(phenyl)acetic acidHCID 178527796HCID 178527796, compound

Product 1

HCID 12928398rac-[(5-Chloro-1,3-benzothiazol-2-yl)thio](phenyl)acetic AcidYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

50.0 g. (0.248 m) 5-chloro-2-mercaptobenzothiazole and 53.0 g. (0.248 m) α-bromophenylacetic acid are dissolved in 1.51. acetone and the solution is heated for 4 hours in the presence of 50 ml. glacial acetic acid. The solution is concentrated to a smaller volume (about 200 ml) and the residual solid (90 g.) is collected. The resulting salt is suspended in 1 l of water and the mixture is stirred at room temperature overnight. The collected solid is recrystallized from 2.5 l. acetonitrile to give a total of 64 g (85% yield) of title compound melting at 190°-2° C.

Workup

  1. concentrationThe solution is concentrated to a smaller volume (about 200 ml)
  2. customthe residual solid (90 g.) is collected
  3. customThe collected solid is recrystallized from 2.5 l

Sources & evidence

ORD record
ord-6f969526aef548cfb670cacc8bcc75fe
Source dataset
uspto-grants-1986_09
Patent number
US04609667

Linked notes

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