Phosphorus oxychloride → methyl 3-chloro-1-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate

HRID 402484

반응식

HRID 402484 반응식
O=P(Cl)(Cl)[Cl:3].O[C:7]1[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[N:9]([CH3:16])[N:8]=1>C(Cl)(Cl)Cl>[Cl:3][C:7]1[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[N:9]([CH3:16])[N:8]=1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178498599HCID 178498599, 화합물

생성물 1

HCID 67209560methyl 3-chloro-1-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate수율 52.2%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

To a solution of POCl3 (31.8 ml, 341 mmol) and Net3 (47.6 ml, 341 mmol) in CHCl3 (100 ml) at −5° C. was added a solution of methyl 3-hydroxy-1-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate (36 g, 228 mmol) in CHCl3 (100 ml). After 1 h at this temperature, the mixture was stirred for another 20 h under warming to rt. Then, the reaction mixture was poured on ice water and extracted with CHCl3. The combined organics were washed with water, dried over Na2SO4 and evaporated under reduced pressure. This yielded the title compound (21 g, 52%) which was used in the next step without further purification. [LCMS RtJ=0.63 min; [M+H]+=177.0, 179.0]

후처리

  1. additionThen, the reaction mixture was poured on ice water
  2. extractionextracted with CHCl3
  3. washThe combined organics were washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-d744a7b091ec495990d10dac49ef6102
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742106B2

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