Benzoyl Peroxide → HCID 14653263, compound

HRID 893313Notes

Reaction equation

HRID 893313 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13](=[O:14])[C:12]2[CH:15]=[CH:16][S:17][C:11]=2[N:10]=[C:9]1[CH3:18].[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:19][C:16]1[S:17][C:11]2[N:10]=[C:9]([CH3:18])[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:13](=[O:14])[C:12]=2[CH:15]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 901565HCID 901565, compound

Product 1

HCID 14653263HCID 14653263, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In chloroform was dissolved 22.85 g of 3,4-dihydro-3-(2-chlorophenyl)-2-methyl-4-oxothieno[2,3-d]pyrimidine, and 19.5 g of N-bromosuccinimide and trace benzoyl peroxide were added to the solution. The mixture was refluxed for 10 hours. After the resulting crystals were removed from the reaction mixture, the solvent was distilled off. The residue was crystallized from hexane-ethyl acetate to give 22.95 g of 3,4-dihydro-6-bromo-3-(2-chlorophenyl)-2-methyl-4-oxothieno[2,3-d]pyrimidine, m.p. 164.5°-166.5° C.

Workup

  1. additionwere added to the solution
  2. temperatureThe mixture was refluxed for 10 hours
  3. customAfter the resulting crystals were removed from the reaction mixture
  4. distillationthe solvent was distilled off
  5. customThe residue was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-8a68d65cb4ef46f6b5eea3eff7707541
Source dataset
uspto-grants-1992_06
Patent number
US05124331

Reaction notes

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