4-Amino-3-nitrophenyl thiocyanate → 4-(Benzylthio)-2-nitroaniline

HRID 614563

反応式

HRID 614563 の反応式
[S:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)[C:2]#N.[BH4-].[Na+].CS(OC[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)=O>CN(C)C=O>[CH2:2]([S:1][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 148757Benzyl mesylateHCID 4311764Sodium borohydride

生成物 1

HCID 135509934-(Benzylthio)-2-nitroaniline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 19.5 g (0.1 mol) 4-thiocyano-2-nitroaniline in 130 ml dimethylformamide is added 3.78 g (0.1 mol) sodium borohydride, all at once. The mixture is stirred for one-half hour, then 15.2 g (0.1 mol) benzyl methanesulfonate in 70 ml dimethylformamide is added. The solution is stirred at 30° for 3 hours, cooled and partitioned between water and dichloromethane. The layers are separated and the aqueous phase reextracted with dichloromethane. The organic phases are combined, washed with aqueous K2CO3, water and saturated NaCl, dried, filtered and stripped to yield 4-(benzyl)sulfenyl-2-nitroaniline.

後処理

  1. stirringThe solution is stirred at 30° for 3 hours
  2. temperaturecooled
  3. custompartitioned between water and dichloromethane
  4. customThe layers are separated
  5. washwashed with aqueous K2CO3, water and saturated NaCl
  6. customdried
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-9ca894cf666d453283d8aac483b14ef1
出典データセット
uspto-grants-1979_03
特許番号
US04145433

関連ノート

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