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2-Chlorobenzenesulfonyl chloride → 8-(2-Chloro-benzenesulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-1,7-dione

HRID 420652
ノート
印刷プレビュー

反応式

HRID 420652 の反応式
[F:1][C:2]([F:23])([F:22])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][C:12]3([CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]3)[C:11]2=[O:21])=[CH:6][CH:5]=1.C([Li])CCC.[Cl:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36](Cl)(=[O:38])=[O:37]>C1COCC1>[Cl:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36]([N:17]1[CH2:18][CH2:19][C:12]2([C:11](=[O:21])[N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:22])[F:23])=[CH:5][CH:6]=3)[CH2:14][CH2:13]2)[CH2:15][C:16]1=[O:20])(=[O:38])=[O:37]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 584784112-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-1,7-dione2 回HCID 178418339Butyllithium

生成物 1

HCID 534652758-(2-Chloro-benzenesulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-1,7-dione収率 31.7%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
-78 °C

実験手順

2-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-1,7-dione (0.105 g), product of example 1 step D), was dissolved in dry THF (10 ml), cooled to −78° C. under an argon atmosphere, treated dropwise with n-butyllithium (1.6 molar solution in hexanes, 0.22 ml) and then stirred for 20 minutes at −78° C. 2-Chlorobenzenesulfonyl chloride (0.074 g) in THF (2 ml) was then added dropwise, the mixture was stirred 15 minutes at −78° C., the cooling bath was removed and stirring was continued for further 75 minutes, allowing the temperature of the reaction mixture to rise to RT. The reaction mixture was then concentrated in vacuo, the residue adsorbed on silica gel and chromatographed on silica gel (AcOEt/heptane, gradient from 0 to 30%) to give the desired product (0.051 g) as an off-white solid. MS (ESI): 503.0 (MH−).

後処理

  1. stirringthe mixture was stirred 15 minutes at −78° C.
  2. customthe cooling bath was removed
  3. stirringstirring
  4. waitwas continued for further 75 minutes
  5. customto rise to RT
  6. concentrationThe reaction mixture was then concentrated in vacuo
  7. customthe residue adsorbed on silica gel and chromatographed on silica gel (AcOEt/heptane, gradient from 0 to 30%)

出典と根拠

ORDレコード
ord-260d9b6221b444c2b188363bbb442e1e
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08097634B2

反応ノート

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