Sodium Methoxide → HCID 19829955, compound

HRID 1493636Notes

Reaction equation

HRID 1493636 reaction equation
[NH2:1][C:2]([NH:4][N:5]([CH2:19][C:20]([O:22]C)=O)[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=[O:3].C[O-].[Na+]>CO>[O:12]([C:9]1[CH:10]=[CH:11][C:6]([N:5]2[CH2:19][C:20](=[O:22])[NH:1][C:2](=[O:3])[NH:4]2)=[CH:7][CH:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 53833003HCID 53833003, compound2×

Product 1

HCID 19829955HCID 19829955, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl [2-(aminocarbonyl)-1-(4-phenoxyphenyl)hydrazino]acetate (Intermediate 77, 550 mg, 0.0017 mol) in methanol (20 ml) was added sodium methoxide (184 mg, 0.0014 mol) and the mixture was stirred for 2 hours then poured into pH6 buffer (70 ml). This was extracted with ethyl acetate (75 ml), dried (MgSO4) and evaporated to give an off-white solid. This was triturated with ethyl acetate-ether and filtered to give the title compound as an off-white solid (90 mg, 19%) m.p. 211°-213° (dec).

Workup

  1. additionthen poured into pH6 buffer (70 ml)
  2. extractionThis was extracted with ethyl acetate (75 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give an off-white solid
  6. customThis was triturated with ethyl acetate-ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-5579f24c398d41d89804c0e07233180c
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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