Dimethylformamide → 2-Nitro-4-[(prop-2-yn-1-yl)sulfanyl]aniline

HRID 1414759Notes

Reaction equation

HRID 1414759 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]#N)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].CN(C)C=O.[BH4-].[Na+].[CH2:21](Br)[C:22]#C>O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:21]#[CH:22])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 4311764Sodium borohydride

Product 1

HCID 203628142-Nitro-4-[(prop-2-yn-1-yl)sulfanyl]aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.85 G. of 1-amino-2-nitro-4-thiocyanatobenzene in 20 ml. dimethylformamide is treated under nitrogen with 1.14 g. sodium borohydride at not greater than 30° C. The mixture is stirred for one hour at 15°-20° C, then treated with 5 ml. of propargyl bromide at 20°-25° C. After a further 3 hours, water is added and the crude product extracted with chloroform. The dried chloroform solution is passed through a column of silica gel to remove a little polar material. Pure 1-amino-2-nitro-4-(prop-2-yn-1-ylthio)benzene is obtained from the eluate.

Workup

  1. customat not greater than 30° C
  2. additiontreated with 5 ml
  3. customat 20°-25° C
  4. waitAfter a further 3 hours
  5. extractionthe crude product extracted with chloroform
  6. customto remove a little polar material

Sources & evidence

ORD record
ord-2583aea77a0548159795ce168041de8d
Source dataset
uspto-grants-1977_01
Patent number
US04002640

Reaction notes

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