N-methylhydroxylamine hydrochloride → HCID 178429719, compound

HRID 1755897Notes

Reaction equation

HRID 1755897 reaction equation
CC(N(C)C)=O.[SH:7][C:8]1[N:13]2[N:14]=[C:15]([C:17]([OH:19])=O)[N:16]=[C:12]2[N:11]=[C:10]([CH3:20])[CH:9]=1.ClC(N(C)C)=C(C)C.Cl.[CH3:30][NH:31][OH:32].C(N(C(C)C)C(C)C)C>CC(N(C)C)=O>[OH:32][N:31]([CH3:30])[C:17]([C:15]1[N:16]=[C:12]2[N:11]=[C:10]([CH3:20])[CH:9]=[C:8]([SH:7])[N:13]2[N:14]=1)=[O:19]

Participants

6

Reactant 4

HCID 77906N-methylhydroxylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 178474718HCID 178474718, compound

Product 1

HCID 178429719HCID 178429719, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
-10 °C

Procedure

7-Mercapto-5-methyl-s-triazolo[1,5-a]pyrimidine-2-carboxylic acid dimethylacetamide (0.99 g) (3.33 mmol) is suspended in 15 ml of absolute dimethylacetamide and treated while stirring with 530 mg (3.96 mmol) of 1-chloro-N,N,2-trimethyl-1-propenamine. After 4 hours the solution is cooled to -10° C. and treated while stirring with 550 mg (6.6 mmol) of N-methylhydroxylamine hydrochloride and 860 mg (6.6 mmol) of ethyl-diisopropylamine. The reaction mixture is stirred at room temperature for 18 hours and subsequently concentrated in a high vacuum. The residue is crystallized using water and recrystallized from dimethylformamide/diethyl ether. There is obtained 0.50 g of N-hydroxy-7-mercapto-N,5-dimethyl-s-triazolo[1,5-a]pyrimidine-2-carboxamide as yellow crystals of melting point 215° C. (dec.).

Workup

  1. additiontreated
  2. additiontreated
  3. concentrationsubsequently concentrated in a high vacuum
  4. customThe residue is crystallized
  5. customrecrystallized from dimethylformamide/diethyl ether

Sources & evidence

ORD record
ord-3175fce3deb24b08b723bc2b7772acbc
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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