Triethylamine → (1-p-Tolyl-1H-pyrazol-4-yl)-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 572069노트

반응식

HRID 572069 반응식
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[CH:6]=1.C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23]>C(Cl)Cl>[Cl:27][C:26]([Cl:29])([Cl:28])[CH2:25][O:24][C:22](=[O:23])[NH:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[CH:6]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 218128244-Amino-1-p-tolyl-1H-pyrazole

생성물 1

HCID 86686685(1-p-Tolyl-1H-pyrazol-4-yl)-carbamic acid 2,2,2-trichloro-ethyl ester수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Intermediate 6b (150 mg, 0.87 mmol) dissolved in DCM (10 mL) was cooled using an ice bath, and then treated sequentially with triethylamine (0.18 mL, 1.30 mmol) and trichloroethyl chloroformate (0.15 mL, 1.08 mmol). The mixture was stirred with cooling for 45 min, then evaporated to dryness. Residue was purified by FCC, eluting with 0-30% ethyl acetate in cyclohexane, to give the title compound as a beige solid (286 mg, 95%). LCMS (Method 3): Rt 4.25 min, m/z 348/350/352 [MH+].

후처리

  1. temperaturewas cooled
  2. temperaturewith cooling for 45 min
  3. customevaporated to dryness
  4. customResidue was purified by FCC
  5. washeluting with 0-30% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-7c0f89589c5d4184b62d1dc9866d800a
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029373B2

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