Dimethylformamide → HCID 86593148, compound

HRID 1816187Notes

Reaction equation

HRID 1816187 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.CN(C=O)C.[Cl-].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[N:24][C:25]2[N:29]([CH3:30])[CH:28]=[CH:27][N+:26]=2[CH3:31])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl-:8].[NH2:1][C:2]1[N:7]=[C:6]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([N:23]=[N:24][C:25]3[N:26]([CH3:31])[CH:27]=[CH:28][N+:29]=3[CH3:30])=[CH:21][CH:22]=2)[CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 655222-Amino-4,6-dichloropyrimidineHCID 988145497404-02-9

Product 1

HCID 86593148HCID 86593148, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.164 g of 2-amino-4,6-dichloropyrimidine (0.001 mol) and 3 ml of dry DMF, 0.251 g (0.001 mol) of 2-(4-amino-phenylazo)-1,3-dimethyl-3H-imidazol-1-ium chloride and 0.138 g (0.001 mol) of potassium carbonate are charged to a fully equipped round-bottomed flask. The mixture is brought for 17 hours to 80° C. with stirring. After cooling, 4 ml of water are added and the precipitate is filtered off. 100 mg of a red powder containing the starting 2-(4-aminophenylazo)-1,3-dimethyl-3H-imidazol-1-ium chloride and the expected product are obtained. The latter, purified by preparative HPLC, has the following UV absorption characteristics:

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate is filtered off
  3. addition100 mg of a red powder containing the starting 2-(4-aminophenylazo)-1,3-dimethyl-3H-imidazol-1-ium chloride

Sources & evidence

ORD record
ord-d640d44530d9469b9dcd16c28318952e
Source dataset
uspto-grants-2005_04
Patent number
US06884266B2

Reaction notes

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