3,4-Dichloroaniline → 2-(3,4-Dichlorophenylamino)-4-methylamino-5-nitro-pyrimidine

HRID 1374653Notes

Reaction equation

HRID 1374653 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[Cl:21])[NH2:17]>S1(CCCC1)(=O)=O>[Cl:13][C:14]1[CH:15]=[C:16]([NH:17][C:2]2[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=2)[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 71472322-chloro-N-methyl-5-nitropyrimidin-4-amine

Product 1

HCID 99013902-(3,4-Dichlorophenylamino)-4-methylamino-5-nitro-pyrimidine

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

6.47 g of 2-chloro-4-methylamino-5-nitro-pyrimidine and 11.7 g of 3,4-dichloro-aniline are heated to 160° C. in 60 ml of sulpholane within 45 minutes in an oil bath. After 40 minutes stirring at this temperature the reaction mixture is cooled and added to 600 ml of ice water. The precipitate is suction filtered, washed repeatedly with water and dried. The residue is stirred for one hour with 100 ml of ethyl acetate, the precipitate is suction filtered, washed with ethyl acetate and dried.

Workup

  1. temperatureis cooled
  2. filtrationfiltered
  3. washwashed repeatedly with water
  4. customdried
  5. stirringThe residue is stirred for one hour with 100 ml of ethyl acetate
  6. filtrationfiltered
  7. washwashed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-ee33a41e375a4ccfa23dccf0fc7a3e94
Source dataset
uspto-grants-2007_01
Patent number
US07166599B2

Reaction notes

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