p-Toluenesulfonic acid → HCID 21536081, compound

HRID 1077250Notes

Reaction equation

HRID 1077250 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([CH2:7][C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)=O.[CH3:20][NH:21][C:22]([NH2:24])=[O:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[CH3:20][N:21]1[C:5]([C:4]2[CH:17]=[CH:18][CH:19]=[C:2]([Cl:1])[CH:3]=2)=[CH:7][C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)=[N:24][C:22]1=[O:23]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 11719MethylureaHCID 2267821,3-bis(3-chlorophenyl)propane-1,3-dione

Product 1

HCID 21536081HCID 21536081, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 38 g. di(m-chlorobenzoyl)methane in 400 ml. glacial acetic acid is added 23 g. N-methylurea and 57 g. p-toluene sulfonic acid. This mixture is refluxed for 24 hours and acetic acid removed by evaporation in vacuo. The residue is treated with 2N. sodium hydroxide till basic, extracted several times with methylene chloride. The combined methylene chloride extracts are then exhaustively extracted with water, dried and evaporated in vacuo to dryness. The residue is crystallized from methylene chloride/diethyl ether and then twice from benzene to obtain 1-methyl-4,6-di(m-chlorophenyl)-pyrimidine-2(1H)-one, m.p. 178°-181°C.

Workup

  1. temperatureThis mixture is refluxed for 24 hours
  2. customacetic acid removed by evaporation in vacuo
  3. additionThe residue is treated with 2N
  4. extractionsodium hydroxide till basic, extracted several times with methylene chloride
  5. extractionThe combined methylene chloride extracts are then exhaustively extracted with water
  6. customdried
  7. customevaporated in vacuo to dryness
  8. customThe residue is crystallized from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-acea7b078cc24d8788e3900335e59a3a
Source dataset
uspto-grants-1976_05
Patent number
US03959471

Reaction notes

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