Water → HCID 22291132, compound

HRID 1369505Notes

Reaction equation

HRID 1369505 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:7]([C:9]1[CH:34]=[CH:33][C:12]([C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH3:32])=[C:20]([NH:22][C:23](=[O:31])[C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[CH:21]=2)=[O:14])=[CH:11][CH:10]=1)#[N:8].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:7]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH3:32])=[C:20]([NH:22][C:23](=[O:31])[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[CH:26][CH:25]=3)[CH:21]=2)=[O:14])=[CH:33][CH:34]=1)#[N:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 9799563HCID 9799563, compound

Product 1

HCID 22291132HCID 22291132, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl bromoacetate (0.023 ml) was added to a suspension of N-[5-(4-cyanobenzamido)-2-methylphenyl]-4-hydroxybenzamide (0.06 g) and potassium carbonate (0.045 g) in DMF (3 ml) and the mixture was stirred and heated to 80° C. for 5 hours. The mixture was poured into water and extracted with ethyl acetate. The organic extract was dried (MgSO4) and evaporated. The residue was triturated under diethyl ether. The resultant solid was dried under vacuum at 55° C. to give the title compound as a solid (0.024 g); NMR Spectrum: (DMSOd6) 2.2 (s, 3H), 3.71 (s, 3H), 4.9 (s, 2H), 7.05 (d, 2H), 7.23 (d, 1H), 7.56 (d, 1H), 7.81 (s, 1H), 7.97 (m, 4H), 8.1 (d, 2H), 9.75 (s, 1H), 10.44 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. customevaporated
  5. customThe residue was triturated under diethyl ether
  6. customThe resultant solid was dried under vacuum at 55° C.

Sources & evidence

ORD record
ord-3fcaed469a7e44dfb87c75dd9a16ef53
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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