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Phosgene → N-(3,5-dimethyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-N-methyl-chloroformamide

HRID 1755050
ノート
印刷プレビュー

反応式

HRID 1755050 の反応式
[C:1]([Cl:4])(Cl)=[O:2].[CH3:5][C:6]1[CH:11]=[C:10]([NH:12][CH3:13])[CH:9]=[C:8]([CH3:14])[C:7]=1/[CH:15]=[CH:16]/[S:17]([N:20]1[CH2:41][CH2:40][C:23]2([N:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]([F:38])([F:37])[F:36])[CH:29]=3)[NH:25][C:24]2=[O:39])[CH2:22][CH2:21]1)(=[O:19])=[O:18].C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH3:5][C:6]1[CH:11]=[C:10]([N:12]([CH3:13])[C:1]([Cl:4])=[O:2])[CH:9]=[C:8]([CH3:14])[C:7]=1/[CH:15]=[CH:16]/[S:17]([N:20]1[CH2:21][CH2:22][C:23]2([N:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]([F:36])([F:38])[F:37])[CH:29]=3)[NH:25][C:24]2=[O:39])[CH2:40][CH2:41]1)(=[O:18])=[O:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 66816601HCID 66816601、化合物

生成物 1

HCID 86672781N-(3,5-dimethyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-N-methyl-chloroformamide収率 85%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 6344
Dichloromethane
溶媒

実験手順

Phosgene (20% solution in toluene, 35 μL, 67 μmol) was added to a mixed solution of 8-[(E)-2-(2,6-dimethyl-4-methylamino-phenyl)-ethenesulfonyl]-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (30 mg, 56 μmol) and triethylamine (15 μL, 84 μmol) in dichloromethane (1.5 ml) and dimethylformamide (0.5 ml) at 0° C. The mixture was stirred at room temperature for three hours, and then quenched with water and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to give N-(3,5-dimethyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-N-methyl-chloroformamide (28 mg, 85%).

後処理

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was sequentially washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate)

出典と根拠

ORDレコード
ord-6eccd0a5883949b9bd4f472c4de9ba87
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09169254B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート