Water → HCID 178470153, 화합물

HRID 2171544

반응식

HRID 2171544 반응식
[C:1]([CH:3]=[C:4]([NH:13][C:14](=O)[O:15]CC)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])#[N:2].[NH:19]([C:21](=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[NH2:20].C(OCC)(=O)C.O>CN1C(=O)CCC1>[Cl:12][C:6]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=1[C:4]1[N:13]=[C:14]([OH:15])[N:20]2[N:19]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:2]=[C:1]2[CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2786935Ethyl 2-hydrazinyl-2-oxoacetateHCID 76754608Ethyl[2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate

생성물 1

HCID 178470153HCID 178470153, 화합물

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
160 °C

실험 절차

3.0 g (10.5 mmol) of ethyl [2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate (Example 128A) and 1.39 g (10.5 mmol) of ethyl hydrazino(oxo)acetate are dissolved in NMP (16 ml) and stirred in a flask with a calcium chloride drying tube at an oil-bath temperature of 160° C. for 4 h. The reaction mixture is cooled to RT and ethyl acetate (150 ml) and water (100 ml) are added. The organic phase is separated off, dried with magnesium sulphate and concentrated. The residue is chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 1:1, then with dichloromethane/methanol 100:1). The crude product is concentrated, mixed with water and stirred for 1 h. The solid is filtered off with suction and dried; 1.31 g (35% of theory) of the product are obtained.

후처리

  1. temperatureThe reaction mixture is cooled to RT
  2. customThe organic phase is separated off
  3. dry with materialdried with magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 1:1
  6. concentrationThe crude product is concentrated
  7. additionmixed with water
  8. stirringstirred for 1 h
  9. filtrationThe solid is filtered off with suction
  10. customdried
  11. custom1.31 g (35% of theory) of the product are obtained

출처 및 근거

ORD 기록
ord-2c5a8f7fcb2a4e1ba7a0b8c834f39929
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051323B2

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