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

HRID 614563Notes

Reaction equation

HRID 614563 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 135509934-(Benzylthio)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9ca894cf666d453283d8aac483b14ef1
Source dataset
uspto-grants-1979_03
Patent number
US04145433

Reaction notes

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