Water → HCID 10800905, compound

HRID 2051148Notes

Reaction equation

HRID 2051148 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[N:15]=[C:14](Cl)[CH:13]=[C:12]([Cl:17])[N:11]=1.O>O1CCCC1>[Cl:9][C:10]1[N:11]=[C:12]([Cl:17])[CH:13]=[C:14]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)[N:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7813p-ToluidineHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 10800905HCID 10800905, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.4 g of p-toluidine was dissolved in 50 ml of tetrahydrofuran, and 5.5 g of 2,4,6-trichloropyrimidine was dropwise added thereto with stirring at room temperature. After being stirred for 1 hour, 200 ml of water was added to the reaction mixture. The crystal thus precipitated was taken out by filtration and dried to obtain 6.6 g of 2,4-dichloro-6-p-toluidinopyrimidine, which had a m.p. of 162° to 166° C. Next, 2.4 g of phenol and 8.6 g of potassium carbonate were dispersed in 30 ml of N,N'-dimethylimidazolin-2-one, and 2.54 g of the previously prepared 2,4-dichloro-6-p-toluidinopyrimidine was added thereto with stirring and then heated at 150° C. for 2 hours. After the reaction solution was cooled, 100 ml of ethyl acetate was added thereto. The solution was then washed with water and extracted. The resulting ethyl acetate extract was concentrated, and methanol was added to the residue for crystallization. Accordingly, 3.4 g of the intended Coupler (12) was obtained, which had a m.p. of 151° to 152° C.

Workup

  1. stirringAfter being stirred for 1 hour
  2. customThe crystal thus precipitated
  3. filtrationwas taken out by filtration
  4. customdried

Sources & evidence

ORD record
ord-06bbb2ceb2cb4b888beda563850c7c3d
Source dataset
uspto-grants-1991_05
Patent number
US05017466

Reaction notes

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