Dimethyl Sulfoxide → HCID 20194680, compound

HRID 653410

Reaction equation

HRID 653410 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.CS(C)=O.[NH2:13][C:14]1[CH:19]=[CH:18][C:17](O)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:8][C:5]1[CH:4]=[N:3][C:2]([C:17]2[CH:18]=[CH:19][C:14]([NH2:13])=[CH:15][C:16]=2[N+:21]([O-:23])=[O:22])=[N:7][CH:6]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 5906412,5-DichloropyrimidineHCID 34174194-Amino-2-Nitrophenol

Product 1

HCID 20194680HCID 20194680, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1.43 g of 2,5-dichloropyrimidine was dissolved in 20 mol of dimethyl sulfoxide. To this solution, a mixture of 1.50 g of 4-amino-2-nitrophenol and 5 ml of water, and 2.69 g of potassium carbonate were added, and the mixture was reacted in the atmosphere of nitrogen gas at a temperature of from 100° to 110° C. for 2 hours. After the completion of the reaction, the reaction product was poured into water, and extracted with methylene chloride. The extract layer was washed with brine and dried over anhydrous sodium sulfate, and purified by silica gel column chromatography, whereby 0.74 g of 4-(5-chloro-2-pyrimidinyl)-3-nitroaniline having a melting point of from 151° to 152° C., was obtained.

Workup

  1. additionwere added
  2. customthe mixture was reacted in the atmosphere of nitrogen gas at a temperature of from 100° to 110° C. for 2 hours
  3. customAfter the completion of the reaction
  4. extractionextracted with methylene chloride
  5. washThe extract layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. custompurified by silica gel column chromatography, whereby 0.74 g of 4-(5-chloro-2-pyrimidinyl)-3-nitroaniline having a melting point of from 151° to 152° C.
  8. customwas obtained

Sources & evidence

ORD record
ord-d7d16c1e695c4613b2736ebd0cc7678f
Source dataset
uspto-grants-1987_06
Patent number
US04677111

Linked notes

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