Dimethylformamide → 2-Nitro-5-[(pyrimidin-2-yl)sulfanyl]aniline

HRID 1415525Notes

Reaction equation

HRID 1415525 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].[SH:18][C:19]1[N:24]=[CH:23][CH:22]=[CH:21][N:20]=1.CN(C)C=O>O>[NH2:1][C:2]1[CH:7]=[C:6]([S:18][C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 178418793HCID 178418793, compound

Product 1

HCID 214827752-Nitro-5-[(pyrimidin-2-yl)sulfanyl]aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.5 g. of 2-amino-4-chloro-1-nitrobenzene, 5.5 g. of potassium carbonate, and 4.5 g. of 2-mercaptopyrimidine in 25 ml. dimethylformamide is heated overnight under nitrogen at 105°-110° C. The mixture is cooled, diluted with water and the product filtered off. Recrystallization from methanol yields 2-amino-1-nitro-4-(pyrimidin-2-ylthio)benzene.

Workup

  1. additionA mixture of 3.5 g
  2. temperatureThe mixture is cooled
  3. filtrationthe product filtered off
  4. customRecrystallization from methanol

Sources & evidence

ORD record
ord-29bfbba4b845423d827ead892c8ed79e
Source dataset
uspto-grants-1977_01
Patent number
US04005202

Reaction notes

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