p-Toluenesulfonic acid → 3-(4-Chloro-3-ethoxycarbonylhydrazonomethylphenyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

HRID 1978853Notes

Reaction equation

HRID 1978853 reaction equation
[NH:1]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[NH2:2].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]2=[O:27])=[CH:11][C:10]=1[CH:28]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:23])([F:25])[F:24])[N:17]([CH3:26])[C:16]2=[O:27])=[CH:11][C:10]=1[CH:28]=[N:2][NH:1][C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 212012252-Chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]benzaldehyde

Product 1

HCID 702311903-(4-Chloro-3-ethoxycarbonylhydrazonomethylphenyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.0 g of ethyl hydrazinecarboxylate was added to a solution of 3.3 g of 3-[4-chloro-3-formylphenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine and 0.1 g of p-toluenesulfonic acid in 150 ml of toluene. After 2 hours, the solution was washed once with water, the organic phase was dried over sodium sulfate and evaporated down and the residue was stirred with petroleum ether. The precipitate was isolated, washed with petroleum ether and dried.

Workup

  1. washthe solution was washed once with water
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. customevaporated down
  4. customThe precipitate was isolated
  5. washwashed with petroleum ether
  6. customdried

Sources & evidence

ORD record
ord-7115392c8f4f4abea9e8aa8819320a7d
Source dataset
uspto-grants-2001_05
Patent number
US06239074B1

Reaction notes

Loading…