Sodium Methoxide → HCID 178490709, compound

HRID 1706492Notes

Reaction equation

HRID 1706492 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O-:21])=[O:20])=[CH:14][CH:13]=1)=[O:8].[Na+].ClC1C=CC(OC)=C(C=1)C(NCCC1C=CC(CC(O)=O)=CC=1)=O.C[O-].[Na+].Cl.[CH2:54]([NH:62][C:63]([NH:65][C:66]([NH2:68])=[NH:67])=[NH:64])[CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>CO.C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1)=[O:8].[CH2:54]([NH:62][C:63]([NH:65][C:66]([NH2:68])=[NH:67])=[NH:64])[CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

7

Reactant 4

HCID 10942334Sodium MethoxideHCID 23453045HCID 23453045, compoundHCID 23681816HCID 23681816, compoundHCID 178479486HCID 178479486, compound

Product 1

HCID 178490709HCID 178490709, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

3.08 g sodium 4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenylacetate (prepared from 4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenylacetic acid and the equivalent amount of sodium methylate in methanol) and 2.0 g 1-phenethylbiguanide hydrochloride are heated under reflux in 100 ml absolute ethanol for 1 hour. Thereafter, the reaction mixture is evaporated to one half of its original volume, the precipitated sodium chloride is filtered off with suction and the filtrate is mixed with diethyl ether. The desired salt crystallizes out slowly and, for purification, is dissolved in ethanol and again precipitated out by the addition of diethyl ether. The salt thus obtained has a melting point of 121°-123° C.

Workup

  1. customThereafter, the reaction mixture is evaporated to one half of its original volume
  2. filtrationthe precipitated sodium chloride is filtered off with suction
  3. additionthe filtrate is mixed with diethyl ether
  4. customThe desired salt crystallizes out slowly and, for purification
  5. dissolutionis dissolved in ethanol
  6. customagain precipitated out by the addition of diethyl ether
  7. customThe salt thus obtained

Sources & evidence

ORD record
ord-16350d0bc9dd4a88af952c24bb5c54f5
Source dataset
uspto-grants-1980_06
Patent number
US04207341

Reaction notes

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