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

HRID 541301ノート

反応式

HRID 541301 の反応式
[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]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 1385274Diethyl dithiophosphate, potassium saltHCID 68288744Methyl 5-cyano-4-cyclobutyl-2-ethylbenzoate2 回

生成物 1

HCID 86672532Methyl 5-carbamothioyl-4-cyclobutyl-2-ethylbenzoate収率 38.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-4262186ea80b404c89eba126a2134b40
出典データセット
uspto-grants-2014_10
特許番号
US08871790B2

反応ノート

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