Acetamide → 3,5-Dihydroxy-4-phenylazo-benzoic acid methyl ester

HRID 616876

Reaction equation

HRID 616876 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][C:9](=[O:11])[C:8]([N:12]=[N:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:7]([OH:20])[CH2:6]1)=[O:4].C(N)(=O)C.BrC1CC(=O)NC1=O.BrBr>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[C:9]([OH:11])[C:8]([N:12]=[N:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:7]([OH:20])[CH:6]=1

Participants

6

Reactant 4

HCID 178AcetamideHCID 24408BromineHCID 38309BromosuccinimideHCID 1360563743-Hydroxy-5-keto-4-phenylazo-3-cyclohexenecarboxylic acid methyl ester

Product 1

HCID 1360597863,5-Dihydroxy-4-phenylazo-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

54.8 G. of 3-hydroxy-5-keto-4-phenylazo-3-cyclohexene-carboxylic acid methyl ester, 12.0 g. of acetamide and 2.0 g. of bromosuccinimide were stirred in 600 ml. of chloroform and treated dropwise with 32.0 g. of bromine dissolved in 400 ml. of chloroform. The reaction temperature was kept below 35° C. Separation of acetamide hydrobromide soon began. The mixture was stirred at room temperature for an additional 30 minutes and the acetamide hydrobromide was removed by filtration. The filtrate was evaporated to dryness and the residue taken up in a small amount of ethanol, removed by filtration under vacuum and washed with ethanol, whereby there was obtained 3,5-dihydroxy-4-phenylazo-benzoic acid methyl ester of melting point 216°-218° C.

Workup

  1. customwas kept below 35° C
  2. customSeparation of acetamide hydrobromide
  3. customthe acetamide hydrobromide was removed by filtration
  4. customThe filtrate was evaporated to dryness
  5. customremoved by filtration under vacuum
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-42277452546140d19318f86d2fa18867
Source dataset
uspto-grants-1978_02
Patent number
US04076810

Linked notes

Loading…