Ethanol → HCID 22238188, compound

HRID 2117338Notes

Reaction equation

HRID 2117338 reaction equation
[CH:1](OCC)(OCC)OCC.[C:11]([NH:19][C:20]1[CH:21]=[CH:22][C:23]([Cl:38])=[C:24]([NH:26][C:27](=[O:37])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[NH2:36])[CH:25]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)C>C(O)(=O)C>[C:11]([NH:19][C:20]1[CH:21]=[CH:22][C:23]([Cl:38])=[C:24]([N:26]2[C:27](=[O:37])[C:28]3[C:29](=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=3)[N:36]=[CH:1]2)[CH:25]=1)(=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 31214Ethyl orthoformateHCID 9908705N-(5-benzamido-2-chlorophenyl)-2-amino-4-methoxybenzamide

Product 1

HCID 22238188HCID 22238188, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Triethyl orthoformate (0.189 ml) was added to a stirred mixture of N-(5-benzamido-2-chlorophenyl)-2-amino-4-methoxybenzamide (0.15 g), ethanol (10 ml) and glacial acetic acid (0.022 ml) and the resultant mixture was heated to 70° C. for 16 hours. The mixture was evaporated. The residue was partitioned between methylene chloride and a saturated aqueous solution of sodium bicarbonate. The organic phase was dried (MgSO4) and evaporated and the residue was triturated under a mixture of ethyl acetate and diethyl ether. The material so obtained was further purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Hengoed, Mid-Glamorgan, UK) using initially methanol and then a 99:1 mixture of methanol and a saturated aqueous ammonium hydroxide solution as eluent. There was thus obtained the title compound (0.054 g); NMR Spectrum: (DMSOd6) 3.92 (s, 3H), 7.12-7.22 (m, 2H), 7.48-7.6 (m, 3H), 7.68 (d, 1H), 7.88-8.0 (m, 3H), 8.04-8.12 (m, 2H), 8.28 (m, 1H), 10.06 (s, 1H); Mass Spectrum: M+H+ 406 and 408.

Workup

  1. customThe mixture was evaporated
  2. customThe residue was partitioned between methylene chloride
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customthe residue was triturated under a mixture of ethyl acetate and diethyl ether
  6. customThe material so obtained
  7. customwas further purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Hengoed, Mid-Glamorgan, UK)
  8. additiona 99:1 mixture of methanol

Sources & evidence

ORD record
ord-50f378dec4af4f909a1c6c0c1a4aa46f
Source dataset
uspto-grants-2008_10
Patent number
US07442704B2

Reaction notes

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