Sodium Methoxide → HCID 86682942, compound

HRID 1497075Notes

Reaction equation

HRID 1497075 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]([NH:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=1[C:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:6].C[O-].[Na+]>CO>[CH3:1][O:2][C:3]([C:4]1[C:5](=[O:6])[NH:7][C:8]2[C:9]([C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:10][C:11]([Cl:15])=[CH:12][C:13]=2[Cl:14])=[O:24]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86682941HCID 86682941, compound

Product 1

HCID 86682942HCID 86682942, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Crude N-(2-benzoyl-4,6-dichloro-phenyl)-malonamic acid methyl ester (600 mg, 1.64 mmol, Eq: 1.00) from step A was suspended in methanol (16 ml) and a solution of sodium methanolate in methanol (13.8 ml, 0.5 M, 6.88 mmol, Eq: 4.2) was added. The reaction mixture was stirred at reflux for 1 h and was then allowed to cool to RT overnight. Most of the methanol was removed in vacuo and the remaining residue was poured onto ice. The mixture was acidified to pH 6 with 1N and 0.1N HCl and a light brown solid precipitated. The solid was filtered off, washed with water and a small amount of MeOH and dried. The resulting title compound (522 mg, light brown solid) was used in the next reaction step without further purification. MS (ESI): 348.0 (M+H)+.

Workup

  1. temperatureat reflux for 1 h
  2. customMost of the methanol was removed in vacuo
  3. additionthe remaining residue was poured onto ice
  4. customa light brown solid precipitated
  5. filtrationThe solid was filtered off
  6. washwashed with water
  7. dry with materiala small amount of MeOH and dried
  8. customThe resulting title compound (522 mg, light brown solid) was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-4e31dd3b2b954e5eb79a7523e15b3062
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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