Dichloromethane → HCID 13560801, compound

HRID 1285506Notes

Reaction equation

HRID 1285506 reaction equation
C(Cl)Cl.[SH:4][C:5]1[S:6][C:7]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:8]=2[N:9]=1.Br[CH:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19]([OH:21])=[O:20]>C(N(CC)CC)C>[N+:14]([C:12]1[CH:11]=[CH:10][C:8]2[N:9]=[C:5]([S:4][CH:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19]([OH:21])=[O:20])[S:6][C:7]=2[CH:13]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 97919Bromo(phenyl)acetic acidHCID 178418579HCID 178418579, compound

Product 1

HCID 13560801HCID 13560801, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A methylene chloride solution of 5.0 g (0.0235 m) 2-mercapto-6-nitrobenzothiazole, 5.2 g (0.0235 m) α-bromophenylacetic acid and 5.0 g (0.05 m) triethylamine is heated to gentle reflux overnight. The solution is washed twice with a dilute hydrochloric acid solution and once with water. The solution is dried over anhydrous MgSO4 and then concentrated. The residue is recrystallized once from benzene and then from acetonitrile. 1.5 g (18% yield) of title compound, having a melting point of 152°-5° C., is obtained.

Workup

  1. temperatureto gentle reflux overnight
  2. washThe solution is washed twice with a dilute hydrochloric acid solution and once with water
  3. dry with materialThe solution is dried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customThe residue is recrystallized once from benzene

Sources & evidence

ORD record
ord-b26a4f3142c946cd9e975c68ad212f38
Source dataset
uspto-grants-1986_01
Patent number
US04567267

Reaction notes

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