Hydrochloric Acid → 5-mercapto-1H-tetrazole-1-propionohydroxamic acid methyl ester

HRID 1584036Notes

Reaction equation

HRID 1584036 reaction equation
[SH:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]([OH:11])=O)[N:5]=[N:4][N:3]=1.Cl.[CH3:13][O:14][NH2:15].C(N(CC)CC)C.Cl>CN(C)C=O>[CH3:13][O:14][NH:15][C:9](=[O:11])[CH2:8][CH2:7][N:6]1[C:2]([SH:1])=[N:3][N:4]=[N:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 178525591HCID 178525591, compound

Product 1

HCID 1785028945-mercapto-1H-tetrazole-1-propionohydroxamic acid methyl esterYield 98.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice cold and stirred solution of 5-mercapto-1H-tetrazole-1-propionic acid (1.04 g) in N,N-dimethylformamide (60 ml) is added N,N'-carbonyldiimidazole (1.16 g). After stirring for 15 minutes at 0° C., the mixture is mixed with a solution of methoxyamine hydrochloride (600 mg) and triethylamine (720 mg) in N,N-dimethylformamide (6 ml) and stirred for 1 hour at 0° C. The reaction mixture is poured into diluted hydrochloric acid and extracted with a mixture of ethyl acetate and methyl ethyl ketone (2:1). The solvent is evaporated from the extract to leave crystalline 5-mercapto-1H-tetrazole-1-propionohydroxamic acid methyl ester (1.2 g). mp. 170°-171° C. (decomp.).

Workup

  1. stirringstirred for 1 hour at 0° C
  2. extractionextracted with a mixture of ethyl acetate and methyl ethyl ketone (2:1)
  3. customThe solvent is evaporated from the
  4. extractionextract

Sources & evidence

ORD record
ord-32bb0034c01645df8dd473f3d9cabf60
Source dataset
uspto-grants-1985_11
Patent number
US04555578

Reaction notes

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