N,N-Dimethylaniline → 2-(4-Nitrophenyl)-ethyl [4-(phenylamino)phenyl]-carbamate

HRID 393510

反応式

HRID 393510 の反応式
Cl[C:2](Cl)([O:4][C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([CH:22](O)C)=[CH:18][CH:17]=1)([O-:15])=[O:14].CN(C)C1C=CC=CC=1.[CH:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=2)=[CH:36][CH:35]=1>ClCCl.C(OCC)C.O>[C:37]1([NH:40][C:41]2[CH:46]=[CH:45][C:44]([NH:47][C:5](=[O:11])[O:4][CH2:2][CH2:22][C:19]3[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=3)=[CH:43][CH:42]=2)[CH:36]=[CH:35][CH:34]=[CH:39][CH:38]=1

参加物

8

反応物 4

HCID 949N,N-Dimethylaniline2 回HCID 7564N-Phenyl-p-phenylenediamineHCID 94429TriphosgeneHCID 5923761-(4-Nitrophenyl)ethan-1-ol

生成物 1

HCID 121468592-(4-Nitrophenyl)-ethyl [4-(phenylamino)phenyl]-carbamate収率 22%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒4 回

反応条件

温度
20 °C

実験手順

1.18 g (3.9 mmol) of triphosgene is dissolved in 15 ml of dichloromethane in a 250 ml flask, under argon,. Using a motorized syringe, a solution of 2 g (12 mmol) of 4-nitrophenylethanol and 1.7 ml (13 mmol) of N,N-dimethylaniline in 40 ml of dichloromethane is added over 1 hour. The reaction mixture is agitated for a few minutes at 20° C. before adding in one go a solution of 2.2 g (12 mmol) of 4-aminodiphenylamine and 1.7 ml (13 mmol) of N,N-dimethylaniline in 40 ml of dichloromethane. After agitation for one hour at 20° C., the contents of the flask are poured into 100 ml of water. The mixture is diluted with 100 ml of dichloromethane and agitated. The organic phase is decanted, dried over magnesium sulphate, filtered and evaporated under vacuum. The solid obtained is taken up in ethyl ether, triturated and filtered. After drying, a greenish powder is obtained with a yield of 22%. Melting point: 146.4-148° C.

後処理

  1. additionbefore adding in one
  2. stirringagitated
  3. customThe organic phase is decanted
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe solid obtained
  8. customtriturated
  9. filtrationfiltered
  10. customAfter drying
  11. customa greenish powder is obtained with a yield of 22%

出典と根拠

ORDレコード
ord-71b404e4407741cc956e2159a2b2afad
出典データセット
uspto-grants-2004_10
特許番号
US06809090B2

関連ノート

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