Water → HCID 136481666, compound

HRID 2073613Notes

Reaction equation

HRID 2073613 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[N:9]2[N:16]=[CH:17][N:18]=[C:8]2[NH:7][C:6]=1[CH3:19])=[O:4].[Br:20]Br.O>C(O)(=O)C>[Br:20][CH2:19][C:6]1[NH:7][C:8]2[N:9]([N:16]=[CH:17][N:18]=2)[CH:10]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 135698649HCID 135698649, compound

Product 1

HCID 136481666HCID 136481666, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

In 300 ml of acetic acid is dissolved 29.5 g of 6-methoxycarbonyl-5-methyl-7-(2-thienyl)-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine at 60° C. To the solution is added dropwise a solution of 16 g of bromine in 50 ml of acetic acid for 20 minutes with stirring. After stirring at room temperature for an hour, the reaction mixture is poured into water, extracted with chloroform, washed with water and potassium carbonate solution, dried and the solvent is evaporated under reduced pressure. The obtained pale yellow crystals are recrystallized from ethanol to give 18 g of 5-bromomethyl-6-methoxycarbonyl-7-(2-thienyl)-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine, melting at 155° C. with decomposition.

Workup

  1. stirringAfter stirring at room temperature for an hour
  2. extractionextracted with chloroform
  3. washwashed with water and potassium carbonate solution
  4. customdried
  5. customthe solvent is evaporated under reduced pressure
  6. customThe obtained pale yellow crystals are recrystallized from ethanol

Sources & evidence

ORD record
ord-1f4011c7f62b4fddbc9f9ee9d6184e14
Source dataset
uspto-grants-1990_04
Patent number
US04918074

Reaction notes

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