Hydrochloric Acid → HCID 178429721, compound

HRID 1755864Notes

Reaction equation

HRID 1755864 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][OH:10].[SH:11][C:12]1[N:17]2[N:18]=[C:19]([C:21](OC)=[O:22])[N:20]=[C:16]2[N:15]=[C:14]([CH3:25])[CH:13]=1.Cl>CO>[OH:10][NH:9][C:21]([C:19]1[N:20]=[C:16]2[N:15]=[C:14]([CH3:25])[CH:13]=[C:12]([SH:11])[N:17]2[N:18]=1)=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 178499048HCID 178499048, compound

Product 1

HCID 178429721HCID 178429721, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Triethylamine (1.35 g) (13.37 mmol) are added dropwise at 0° C. to a solution of 0.62 g (8.92 mmol) of hydroxylamine hydrochloride in 15 ml of absolute methanol. The mixture is stirred for 10 minutes and subsequently a solution of 1.0 g (4.46 mmol) of methyl 7-mercapto-5-methyl-s-triazolo[1,5-a]pyrimidine-2-carboxylate (known from EPOS 303,172) in 30 ml of absolute methanol is added dropwise. After stirring at room temperature for 3 days the beige suspension is made acid (pH 4) with 1N aqueous hydrochloric acid and suction filtered. The filter material is washed with water and diethyl ether and crystallized from methanol/dichloromethane. There are obtained 510 mg of N-hydroxy-7-mercapto-5-methyl-s-triazolo[1,5-a]pyrimidine-2-carboxamide as beige crystals of m.p. 213° C. (dec.).

Workup

  1. stirringAfter stirring at room temperature for 3 days the beige suspension
  2. filtrationfiltered
  3. washThe filter material is washed with water and diethyl ether
  4. customcrystallized from methanol/dichloromethane

Sources & evidence

ORD record
ord-2e0e379a95864408b3b4859324989aec
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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