Dimethyl Sulfoxide → N-[2-(4,5,7-trifluorobenzothiazol-2-ylthio)acetyl]-N-phenylglycine

HRID 1940621Notes

Reaction equation

HRID 1940621 reaction equation
CS(C)=O.[F:5][C:6]1[C:11]2[N:12]=[C:13]([S:15][CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:18])[S:14][C:10]=2[C:9]([F:26])=[CH:8][C:7]=1[F:27].Br[CH2:29][C:30]([OH:32])=[O:31].C(=O)([O-])[O-].[K+].[K+]>O>[F:5][C:6]1[C:11]2[N:12]=[C:13]([S:15][CH2:16][C:17]([N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:29][C:30]([OH:32])=[O:31])=[O:18])[S:14][C:10]=2[C:9]([F:26])=[CH:8][C:7]=1[F:27]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6227Bromoacetic AcidHCID 11430Potassium CarbonateHCID 214635402-(4,5,7-trifluorobenzothiazol-2-ylthio)-N-phenylacetamide

Product 1

HCID 21463534N-[2-(4,5,7-trifluorobenzothiazol-2-ylthio)acetyl]-N-phenylglycineYield 19.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To DMSO (5 ml) was added 2-(4,5,7-trifluorobenzothiazol-2-ylthio)-N-phenylacetamide (354 mg, 1 mmol), bromoacetic acid (278 mg, 2 mmol) and potassium carbonate (414 mg, 3 mmol) and the mixture was stirred at room temperature for 5 hours under a nitrogen stream. The resultant reaction mixture was diluted with water and washed with ethyl acetate. The aqueous phase was acidified with 7% hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water, dried and then evaporated to yield crude crystals, which were recrystallized from ethyl acetate-hexane to give N-[2-(4,5,7-trifluorobenzothiazol-2-ylthio)acetyl]-N-phenylglycine (80 mg, 19%) as slightly yellow crystals.

Workup

  1. customThe resultant reaction mixture
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated
  7. customto yield crude crystals, which
  8. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-642d5fff46b94ead8fb595727f386a5f
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

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