Acetonitrile → N-[8-chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidin-5-yl]acetamide

HRID 622099Notes

Reaction equation

HRID 622099 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)(O)[C:7]3[CH:12]=[N:11][CH:10]=[N:9][C:8]=32)=[CH:4][CH:3]=1.C(=O)(O)[O-:24].[K+].[C:28](#[N:30])[CH3:29]>CS(O)(=O)=O>[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]([NH:30][C:28](=[O:24])[CH3:29])([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[C:7]3[CH:12]=[N:11][CH:10]=[N:9][C:8]=32)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 516893Potassium BicarbonateHCID 142570878-chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidin-5-ol

Product 1

HCID 14257092N-[8-chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidin-5-yl]acetamide

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A mixture of 3.0 g of 8-chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidin-5-ol in 15 ml of acetonitrile and 50 ml of methanesulfonic acid were stirred for approximately 18 hours. The reaction mixture was added to a large excess of a potassium bicarbonate solution and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. Crystallization from acetonitrile/water provided 2.53 g of the desired title product, m.p. 238°-241° C. Two further recrystallizations provided material with a melting point of 245°-248° C.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customCrystallization from acetonitrile/water

Sources & evidence

ORD record
ord-9e73b667e8c84cd48ce28747039a3937
Source dataset
uspto-grants-1988_09
Patent number
US04769378

Reaction notes

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