Dimethylformamide → 2-Nitro-4-[(pyridin-2-yl)sulfanyl]aniline

HRID 1580956Notes

Reaction equation

HRID 1580956 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]#[N:13])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=O)C.CN(C)C=O.[BH4-].[Na+].BrC1[CH:30]=[CH:29][CH:28]=[CH:27]N=1>O>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[CH:30]=[CH:29][CH:28]=[CH:27][N:13]=2)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79732-BromopyridineHCID 4311764Sodium borohydrideHCID 8180927Thiocyanic acid, 4-(acetylamino)-3-nitrophenyl ester

Product 1

HCID 214827702-Nitro-4-[(pyridin-2-yl)sulfanyl]aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 5.85 g. of 1-acetamido-2-nitro-4-thiocyanatobenzene in 20 ml. dimethylformamide is cooled, under nitrogen, to about 0°C. and 1.14 g. of sodium borohydride is added. The exothermic reaction is controlled to less than about 30°C., then the mixture is stirred for 1 hour at 20°-30°C. 6 Ml. of 2-bromopyridine is added and the mixture warmed slowly to about 110°C. and kept at that temperature for 1 hour. The mixture is cooled, diluted with water, and filtered. The crude product is recrystallized from aqueous methanol, yielding 1-amino-2-nitro-4-(pyrid-2-ylthio)benzene.

Workup

  1. customThe exothermic reaction
  2. customis controlled to less than about 30°C.
  3. waitkept at that temperature for 1 hour
  4. temperatureThe mixture is cooled
  5. filtrationfiltered
  6. customThe crude product is recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-5e68173f7f8c4f22ad6b85ef0c8d9f89
Source dataset
uspto-grants-1976_01
Patent number
US03935209

Reaction notes

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