Water → HCID 178502684, compound

HRID 2368469Notes

Reaction equation

HRID 2368469 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[C:9]2[SH:16])=[CH:4][CH:3]=1.[CH3:17][NH:18][O:19][CH3:20].C(N=C=NCCCN(C)C)C.O>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([N:18]([O:19][CH3:20])[CH3:17])=[O:15])=[CH:11][N:10]=[C:9]2[SH:16])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14232N,O-DimethylhydroxylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 178524781HCID 178524781, compound

Product 1

HCID 178502684HCID 178502684, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-(4-fluorophenyl)-2-mercapto-1H-imidazole-5-carboxylic acid (4) (2.2 g, 9.23 mmol), N,O-dimethylhydroxylamine (0.9 g, 9.23 mmol), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) (1.77 g, 9.23 mmol) in pyridine was heated at 40° C. overnight. The reaction was cooled to room temperature, water was added and the solution was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to yield 1-(4-fluorophenyl)-2-mercapto-N-methoxy-N-methyl-1H-imidazole-5-carboxamide (5) as a light yellow solid.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ddaa5fe9fc7943caaf773758245c2802
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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