1,3,2,4-Dithiadiphosphetane, 2,4-bis(methylthio)-, 2,4-disulfide → (S)-methyl 3,4-dihydro-2,8-diisopropyl-3-thioxo-2H-1,4-benzoxazine-4-acetate

HRID 622371ノート

反応式

HRID 622371 の反応式
[CH:1]([C@H:4]1[C:9](=O)[N:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:7]2[CH:16]=[CH:17][CH:18]=[C:19]([CH:20]([CH3:22])[CH3:21])[C:6]=2[O:5]1)([CH3:3])[CH3:2].C[S:24]P1(=S)SP(=S)(SC)S1>C1(C)C=CC=CC=1>[CH:1]([C@H:4]1[C:9](=[S:24])[N:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:7]2[CH:16]=[CH:17][CH:18]=[C:19]([CH:20]([CH3:22])[CH3:21])[C:6]=2[O:5]1)([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 45209581,3,2,4-Dithiadiphosphetane, 2,4-bis(methylthio)-, 2,4-disulfideHCID 14234720(S)-methyl 3,4-dihydro-2,8-diisopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate

生成物 1

HCID 22839825(S)-methyl 3,4-dihydro-2,8-diisopropyl-3-thioxo-2H-1,4-benzoxazine-4-acetate収率 93.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
50 °C

実験手順

A mixture of (S)-methyl 3,4-dihydro-2,8-diisopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate (3.05 g), 2,4-bis (methylthio)-1,3,2,4-dithiadiphosphetan-2,4-disulfide (Davy reagent methyl)(2.84 g) and toluene (60 ml) was stirred at 50° C. for 64 hours. The insoluble material was filtered off and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (100 g) using hexane-ethyl ether (85:15, v/v) as the eluent to yield (S)-methyl 3,4-dihydro-2,8-diisopropyl-3-thioxo-2H-1,4-benzoxazine-4-acetate as an oil (3.00 g).

後処理

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel (100 g)

出典と根拠

ORDレコード
ord-197c87abe532419fa93d5c5c3b370478
出典データセット
uspto-grants-1988_09
特許番号
US04771050

反応ノート

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