Dichloromethane → alpha-Phenyl-alpha-[(4,5,6,7-tetrahydrobenzothiazol-2-yl)thio]acetic acid

HRID 1285505Notes

Reaction equation

HRID 1285505 reaction equation
C(Cl)Cl.[SH:4][C:5]1[S:6][C:7]2[CH2:13][CH2:12][CH2:11][CH2:10][C:8]=2[N:9]=1.Br[CH:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16]([OH:18])=[O:17]>C(N(CC)CC)C>[C:19]1([CH:15]([S:4][C:5]2[S:6][C:7]3[CH2:13][CH2:12][CH2:11][CH2:10][C:8]=3[N:9]=2)[C:16]([OH:18])=[O:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 97919Bromo(phenyl)acetic acidHCID 1785278174,5,6,7-Tetrahydro-1,3-benzothiazole-2-thiol

Product 1

HCID 13560800alpha-Phenyl-alpha-[(4,5,6,7-tetrahydrobenzothiazol-2-yl)thio]acetic acidYield 77%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A methylene chloride solution of 5.13 g (0.03 m) 2-mercapto-4,5,6,7-tetrahydrobenzothiazole, 6.45 g. (0.03 m) α-bromophenylacetic acid and 6.0 g (0.06 m) triethylamine is heated to gentle reflux overnight. The solution is extracted twice with a dilute hydrochloric acid solution, once with water and is then dried over anhydrous MgSO4. The residual solid after solvent removal is recrystallized from acetonitrile. 7.0 g (77% yield) of title compound, melting at 118°-20° C., is obtained

Workup

  1. temperatureto gentle reflux overnight
  2. extractionThe solution is extracted twice with a dilute hydrochloric acid solution, once with water
  3. dry with materialis then dried over anhydrous MgSO4
  4. customThe residual solid after solvent removal
  5. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-92a1df7ce37a479d824f7170e6c77799
Source dataset
uspto-grants-1986_01
Patent number
US04567267

Reaction notes

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