Dimethylcarbamoyl Chloride → 5-Bromosalicylhydroxamic Acid N,N-Dimethylcarbamate

HRID 980428Notes

Reaction equation

HRID 980428 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:18]=[C:13]([C:14]([NH:16][OH:17])=[O:15])[C:12]([OH:19])=[CH:11][CH:10]=1.[CH3:20][N:21]([CH3:25])[C:22](Cl)=[O:23]>CN(C)C=O>[CH3:20][N:21]([CH3:25])[C:22](=[O:15])[OH:23].[Br:8][C:9]1[CH:18]=[C:13]([C:14]([NH:16][OH:17])=[O:15])[C:12]([OH:19])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 220465-Bromosalicylhydroxamic acid2×

Product 1

HCID 867412175-Bromosalicylhydroxamic Acid N,N-Dimethylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

81 ml of triethylamine was gradually added to a dimethylformamide solution containing 136 g of 5-bromosalicylhydroxamic acid prepared as in (2-2) above and 54 ml of N,N-dimethylcarbamyl chloride at room temperature (about 20°-30° C.), then stirred for 10 hours. This solution was poured into ice-water to collect the precipitate by filtration followed by drying. Yield: 102 g; mp. 118°-119° C. (dec.)

Workup

  1. additioncontaining
  2. customto collect the precipitate
  3. filtrationby filtration
  4. customby drying

Sources & evidence

ORD record
ord-12510d497a8c4a0194d2eb60ff0048ea
Source dataset
uspto-grants-1987_01
Patent number
US04637902

Reaction notes

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