Bromo(phenyl)acetic acid → HCID 13060849, compound

HRID 2286275Notes

Reaction equation

HRID 2286275 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[S:6].[Br:7][CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9](O)=[O:10]>C(O)(=O)C>[Br-:7].[OH:10][C:9]1[N+:1]2[CH2:5][CH2:4][CH2:3][C:2]=2[S:6][C:8]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 97919Bromo(phenyl)acetic acidHCID 27752672-Pyrrolethione, tetrahydro-, (Z)-

Product 1

HCID 13060849HCID 13060849, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 50 ml. glacial acetic acid solution of 3.0 g. (0.03 m.) 2-pyrrolidinethione and 6.5 g. (0.03 m.) α-bromophenylacetic acid is heated on a steam bath for 5 hours. The solution is cooled and the precipitated solid is collected and washed with acetone and ether. The 7.0 g. of solid is recrystallized from acetonitrile to give 4.2 g. (47% yield) of title compound, m.p. 200°-205° C.

Workup

  1. temperatureThe solution is cooled
  2. customthe precipitated solid is collected
  3. washwashed with acetone and ether
  4. customof solid is recrystallized from acetonitrile
  5. customto give 4.2 g

Sources & evidence

ORD record
ord-5fd7b0d67fc14b038d6d76563961c187
Source dataset
uspto-grants-1982_04
Patent number
US04327221

Reaction notes

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