Dichloromethane → HCID 20249365, compound

HRID 1163885Notes

Reaction equation

HRID 1163885 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][CH:23]=[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][CH:23]=[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 97919Bromo(phenyl)acetic acidHCID 178527792HCID 178527792, compound

Product 1

HCID 20249365HCID 20249365, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A methylene chloride solution of 4.05 g (0.02 m) 5-chloro-2-mercaptothiazolo[5,4-b]pyridine, 4.30 g (0.02 m) α-bromophenylacetic acid and 4.0 g (0.04 m) triethylamine is heated to gentle reflux overnight. The methylene chloride solution is extracted twice with a dilute hydrochloric acid solution and once with water and then dried over anhydrous MgSO4. After the solvent is removed, the residual solid is recrystallized from acetonitrile. 5.0 g (74% yield) of title compound, melting at 175°-7° C., is obtained.

Workup

  1. temperatureto gentle reflux overnight
  2. extractionThe methylene chloride solution is extracted twice with a dilute hydrochloric acid solution and once with water
  3. dry with materialdried over anhydrous MgSO4
  4. customAfter the solvent is removed
  5. customthe residual solid is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-482b3cdb39a34cfebcdc1215fa3d6dab
Source dataset
uspto-grants-1983_01
Patent number
US04367233

Reaction notes

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