Sodium Chloride → HCID 86736103, compound

HRID 28175Notes

Reaction equation

HRID 28175 reaction equation
[Na].C[O-].[Na+].[ClH:5].[NH2:6][OH:7].[Cl-].[Na+].[NH2:10][C:11]1[CH:25]=[CH:24][C:14]([C:15]([NH:17][CH2:18][C:19](OCC)=[O:20])=[O:16])=[CH:13][CH:12]=1>CO>[ClH:5].[NH2:10][C:11]1[CH:25]=[CH:24][C:14]([C:15]([NH:17][CH2:18][C:19]([NH:6][OH:7])=[O:20])=[O:16])=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 12469740Ethyl 4-aminobenzamidoacetate

Product 1

HCID 86736103HCID 86736103, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5.75 g (0.25 gram atom) of sodium are added in small pieces to 150 ml of anhydrous methanol, and this cold solution of sodium methylate is then poured into a solution of 10.5 g (0.15 mol) of hydroxylamine hydrochloride in 100 ml of anhydrous methanol. The mixture is stirred for half an hour in the cold, the sodium chloride precipitate is filtered off and 22.2 g (0.1 mol) of ethyl 4-aminobenzamidoacetate are added to the filtrate; after leaving the reactants in contact overnight, the mixture is evaporated to dryness in vacuo, the residue is taken up in 100 ml of water and the hydrochloride is precipitated by adding 6 N HCl up to pH=1, and is filtered off and washed with 10 ml of cold water. CRL 40,473 is thus obtained by recrystallisation from a 4:1 (volume/volume) mixture of methanol and water. Melting point 182°-185° C. (with decomposition). Yield: 72%.

Workup

  1. filtrationis filtered off
  2. customafter leaving the reactants in contact overnight
  3. customthe mixture is evaporated to dryness in vacuo
  4. customthe hydrochloride is precipitated
  5. additionby adding 6 N HCl up to pH=1
  6. filtrationis filtered off
  7. washwashed with 10 ml of cold water
  8. customCRL 40,473 is thus obtained by recrystallisation from a 4:1 (volume/volume) mixture of methanol and water

Sources & evidence

ORD record
ord-02ef43f92ae143b8999d24ccc72178d6
Source dataset
uspto-grants-1980_09
Patent number
US04225617

Reaction notes

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