Sodium Chloride → HCID 20183383, compound

HRID 255724Notes

Reaction equation

HRID 255724 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([NH2:25])=O.[Cl-].[Na+].P(Cl)(Cl)(Cl)=O>ClCCCl>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]#[N:25]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 24813Phosphorus oxychlorideHCID 11724425HCID 11724425, compound

Product 1

HCID 20183383HCID 20183383, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxamide (10 g), sodium chloride (8 g) and phosphorous oxychloride (3.3 g) in 1,2-dichloroethane (50 ml) was refluxed for 10 hours. After removal of the sodium chloride, the reaction mixture was poured into a mixture of dichloromethane (200 ml) and aqueous saturated hydrogen carbonate solution (100 ml). The separated organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from diethyl ether, collected, washed with diethyl ether and dried to give 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarbonitrile (6.3 g).

Workup

  1. temperaturewas refluxed for 10 hours
  2. customAfter removal of the sodium chloride
  3. additionthe reaction mixture was poured into a mixture of dichloromethane (200 ml) and aqueous saturated hydrogen carbonate solution (100 ml)
  4. dry with materialThe separated organic layer was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from diethyl ether
  7. customcollected
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-07b5bf4289ec46cc9f0d215685ed7a8f
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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