Dimethylformamide → (2Z)-2-[2-(dimethylaminomethylideneamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetyl chloride;hydrochloride

HRID 266247

반응식

HRID 266247 반응식
[CH3:1][N:2]([CH3:5])[CH:3]=O.[Cl:6]C([O:9][C:10]([Cl:13])(Cl)Cl)=O.[NH2:14][C:15]1[S:16][CH:17]=[C:18](/[C:20](=[N:24]/[O:25][CH3:26])/C(O)=O)[N:19]=1.C(OC(C)C)(=O)C>O1CCCC1>[ClH:6].[CH3:1][N:2]([CH:3]=[N:14][C:15]1[S:16][CH:17]=[C:18](/[C:20](=[N:24]/[O:25][CH3:26])/[C:10]([Cl:13])=[O:9])[N:19]=1)[CH3:5]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7915Isopropyl AcetateHCID 10426DiphosgeneHCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acid

생성물 1

HCID 140382097(2Z)-2-[2-(dimethylaminomethylideneamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetyl chloride;hydrochloride수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Dimethylformamide (0.8 g, 11 mmol) was added to 9 ml of tetrahydrofuran, followed by ice-cooling. To the resulting mixture, 0.6 ml of trichloromethyl chloroformate was added dropwise under ice-cooling. After stirring the resulting mixture for 30 minutes, the mixture was cooled to -10° C. (Z)-2-(2-Amino-thiazol-4-yl)-2-methoxyiminoacetic acid (840 mg, 4.2 mmol) was added and the mixture so obtained was stirred for 2 hours. The mixture was added with 9 ml of isopropyl acetate, followed by stirring for 30 minutes. A precipitate was collected by filtration under a nitrogen gas stream and then dried at room temperature, whereby 1.23 g of the title compound were obtained (yield: 94%).

후처리

  1. temperaturecooling
  2. temperaturecooling
  3. additionwas added
  4. customthe mixture so obtained
  5. stirringwas stirred for 2 hours
  6. stirringby stirring for 30 minutes
  7. filtrationA precipitate was collected by filtration under a nitrogen gas stream
  8. customdried at room temperature

출처 및 근거

ORD 기록
ord-a0f791409a584fea8fb7fb0116e3a933
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650518

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