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

HRID 1940621ノート

反応式

HRID 1940621 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-642d5fff46b94ead8fb595727f386a5f
出典データセット
uspto-grants-1997_12
特許番号
US05700819

反応ノート

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