O-Phenylenediamine → 1-(4-Cyano-phenyl)-3-[-(1-phenyl-ethylamino)-phenyl]-urea

HRID 49016

反応式

HRID 49016 の反応式
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].C(=O)([O-])[O-].[K+].[K+].Br[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17].[C:24]([C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=1)#[N:25]>CN(C)C=O>[C:24]([C:26]1[CH:27]=[CH:28][C:29]([NH:32][C:33]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])=[O:34])=[CH:30][CH:31]=1)#[N:25]

参加物

6

反応物 4

HCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 11454(1-Bromoethyl)benzeneHCID 1703804-Cyanophenyl isocyanate

生成物 1

HCID 120439691-(4-Cyano-phenyl)-3-[-(1-phenyl-ethylamino)-phenyl]-urea

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1.16 g (10.8 mmol) 1,2-phenylene diamine was dissolved in 10 ml dimethyl formamide, 2.1 g (15 mmol) potassium carbonate and 1.47 ml (10.8 mmol) 1-bromo-1-phenylethane were added with stirring. After 8 hours (h) at rt, most of the starting materials were consumed. Potassium bromide was filtered off, the solvent removed, the mixture redissolved in 20 ml THF and then 1,15 g (8 mmol) 4-cyanophenylisocyanate were slowly added and stirred for another 50 h at rt. The mixture was worked up by filtration, evaporated to dryness, dissolved in ethyl acetate and washed with diluted HCl, sodium carbonate solution and brine.

後処理

  1. custommost of the starting materials were consumed
  2. filtrationPotassium bromide was filtered off
  3. customthe solvent removed
  4. dissolutionthe mixture redissolved in 20 ml THF
  5. stirringstirred for another 50 h at rt
  6. filtrationThe mixture was worked up by filtration
  7. customevaporated to dryness
  8. dissolutiondissolved in ethyl acetate
  9. washwashed with diluted HCl, sodium carbonate solution and brine

出典と根拠

ORDレコード
ord-76d8bb49b18e460c92fe6379f655d37e
出典データセット
uspto-grants-2004_03
特許番号
US06706715B2

関連ノート

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