Chloroform → HCID 13589482, compound

HRID 2073619Notes

Reaction equation

HRID 2073619 reaction equation
S(Cl)(Cl)=O.[C:5]([C:8]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[N:12]2[CH:23]=[CH:24][N:25]=[C:11]2[NH:10][C:9]=1[CH3:26])(=O)[NH2:6].C(Cl)(Cl)Cl>CN(C)C=O>[C:5]([C:8]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[N:12]2[CH:23]=[CH:24][N:25]=[C:11]2[NH:10][C:9]=1[CH3:26])#[N:6]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 13589481HCID 13589481, compound

Product 1

HCID 13589482HCID 13589482, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 ml of thionyl chloride is added dropwise to a solution of 3 g of 6-carbamoyl-7-methyl-5-(3-nitrophenyl)-5,8-dihydroimidazo[1,2-a]pyrimidine in 30 ml of dimethylformamide. After stirring for an hour, the mixture is poured into chloroform and washed with sodium bicarbonate solution followed by passing the mixture through a column containing 50 g of silica gel with a mixture of dichloromethane and ethanol as an eluent. Upon allowing the eluates to stand, crystals are precipitated and collected by filtration to give 1.1 g of 6-cyano-7-methyl-5-(3-nitrophenyl)-5,8-dihydroimidazo[1,2-a]pyrimidine, melting at 278°-280° C. with decomposition.

Workup

  1. washwashed with sodium bicarbonate solution
  2. additioncontaining 50 g of silica gel
  3. additionwith a mixture of dichloromethane and ethanol as an eluent
  4. customcrystals are precipitated
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5e94871056274164903923d1c1ded62d
Source dataset
uspto-grants-1990_04
Patent number
US04918074

Reaction notes

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