Dichloromethane → HCID 20249370, compound

HRID 1285504Notes

Reaction equation

HRID 1285504 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[N:10]=[C:9]2[S:11][C:12]([SH:14])=[N:13][C:8]2=[CH:7][CH:6]=1.Br[CH:16]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:17]([OH:19])=[O:18]>C(N(CC)CC)C>[Cl:4][C:5]1[N:10]=[C:9]2[S:11][C:12]([S:14][CH:16]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[C:17]([OH:19])=[O:18])=[N:13][C:8]2=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10490868alpha-Bromo-4-chlorophenylacetic acidHCID 178527792HCID 178527792, compound

Product 1

HCID 20249370HCID 20249370, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A methylene chloride solution of 6.0 g (0.03 m) of 5-chloro-2-mercaptothiazolo[5,4-b]pyridine, 7.5 g (0.03 m) α-bromo-α-(p-chlorophenyl)acetic 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 and then once with water. After drying over anhydrous MgSO4, the solvent is removed and the residual solid is recrystallized from acetonitrile. 7.5 g (68% yield) of title compound, melting at 144°-6° C., is obtained.

Workup

  1. temperatureto gentle reflux overnight
  2. extractionThe solution is extracted twice with a dilute hydrochloric acid solution
  3. dry with materialAfter drying over anhydrous MgSO4
  4. customthe solvent is removed
  5. customthe residual solid is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-a7c28604ed34431da5136a4536991298
Source dataset
uspto-grants-1986_01
Patent number
US04567267

Reaction notes

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