Tetrahydrofuran → Methyl 5-carbamothioyl-4-cyclobutyl-2-ethylbenzoate

HRID 541301노트

반응식

HRID 541301 반응식
[C:1]([C:3]1[C:4]([CH:15]2[CH2:18][CH2:17][CH2:16]2)=[CH:5][C:6]([CH2:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].O1CCCC1.P(OCC)(OCC)([S-])=[S:25]>O>[C:1]([C:3]1[C:4]([CH:15]2[CH2:16][CH2:17][CH2:18]2)=[CH:5][C:6]([CH2:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])(=[S:25])[NH2:2]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 1385274Diethyl dithiophosphate, potassium saltHCID 68288744Methyl 5-cyano-4-cyclobutyl-2-ethylbenzoate2회

생성물 1

HCID 86672532Methyl 5-carbamothioyl-4-cyclobutyl-2-ethylbenzoate수율 38.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a round-bottom flask was added a solution of methyl 5-cyano-4-cyclobutyl-2-ethylbenzoate (compound 181.5, 3.00 g, 12.3 mmol, 1.00 equiv) in a solvent mixture of tetrahydrofuran and H2O (80 mL/40 mL). To this was added O,O′-diethyl dithiophosphate (6.69 g, 35.9 mmol, 3.00 equiv) dropwise with stirring. The resulting solution was stiffed at 85° C. for 48 h (CAUTION: significant gas evolution occurs—this and all other reactions described herein should be carried out in well ventilated fume hoods). After cooling to ambient temperature, the mixture was then concentrated in vacuo. The crude product was purified by re-crystallization from petroleum ether to furnish 1.30 g (38%) of methyl 5-carbamothioyl-4-cyclobutyl-2-ethylbenzoate as a light yellow solid.

후처리

  1. concentrationthe mixture was then concentrated in vacuo
  2. customThe crude product was purified by re-crystallization from petroleum ether

출처 및 근거

ORD 기록
ord-4262186ea80b404c89eba126a2134b40
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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