Hydrochloric Acid → HCID 178491620, compound

HRID 1584033Notes

Reaction equation

HRID 1584033 reaction equation
[SH:1][C:2]1[N:6]([CH2:7][C:8]([OH:10])=O)[N:5]=[N:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([CH2:17][O:18][NH2:19])=[CH:15][CH:14]=1.Cl>CN(C)C=O>[CH3:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([CH2:17][O:18][NH:19][C:8](=[O:10])[CH2:7][N:6]2[C:2]([SH:1])=[N:3][N:4]=[N:5]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 120426O-((4-Methoxyphenyl)methyl)hydroxylamineHCID 178525857HCID 178525857, compound

Product 1

HCID 178491620HCID 178491620, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To an ice cold solution of 5-mercapto-1H-tetrazole-1-acetic acid (4.4 g) in N,N-dimethylformamide (40 ml) is added N,N'-carbonyldiimidazole (4.86 g), and the mixture is stirred under nitrogen for 1 hour. To this solution is added a solution of p-methoxybenzyloxyamine (7.9 g) in N,N-dimethylformamide (10 ml), and the mixture is stirred under ice cooling for 45 minutes. The reaction mixture is poured onto ice water containing hydrochloric acid and extracted with ethyl acetate. The extract solution is washed with water, dried and concentrated under reduced pressure. The residue is crystallized from a mixture of acetone and ether to give the title compound (7.3 g). mp. 167°-168° C.

Workup

  1. stirringthe mixture is stirred under ice cooling for 45 minutes
  2. additionThe reaction mixture is poured onto ice water
  3. extractionextracted with ethyl acetate
  4. washThe extract solution is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is crystallized from a mixture of acetone and ether

Sources & evidence

ORD record
ord-d95914d122a24f16a14d4d613068890a
Source dataset
uspto-grants-1985_11
Patent number
US04555578

Reaction notes

Loading…