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

HRID 614563노트

반응식

HRID 614563 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 135509934-(Benzylthio)-2-nitroaniline

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ca894cf666d453283d8aac483b14ef1
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04145433

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