HCID 20296014, compound → HCID 20295984, compound

HRID 1389939Notes

Reaction equation

HRID 1389939 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([NH:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1)[C:10](N)=[O:11].[OH-].[K+].C([OH:28])C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([C:10]([OH:28])=[O:11])[NH:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1

Participants

3

Reactant 2

HCID 20296014HCID 20296014, compoundHCID 21946426Potassium hydroxide ethanol

Product 1

HCID 20295984HCID 20295984, compound

Procedure

A mixture of 12.7 parts of 2-(2,6-dichlorophenyl)-2-(2-naphthylamino) acetamide and 250 parts of potassium hydroxide/ethanol 1 N is stirred and refluxed for 48 hours. The reaction mixture is evaporated. The oily residue is dissolved in 400 parts of water and the solution is acidified with concentrated hydrochloric acid solution. The sticky product is extracted with 1,1'-oxybisethane. The extract is washed twice with water, dried and evaporated. The oily residue is triturated three times in petroleumether. The solid product is filtered off and recrystallized from 50 parts of glacial acetic acid. The product is washed with petroleumether, dried and dissolved in 80 parts of 1,1'-oxybisethane. The solution is stirred with activated charcoal, filtered and the filtrate is evaporated. The oily residue solidifies on triturating in 2-propanol and petroleumether. The solid is filtered off and dried, yielding 1.6 parts of 2-(2,6-dichlorophenyl)-N-(2-naphthyl)glycine; mp. 171.7° C.

Workup

  1. temperaturerefluxed for 48 hours
  2. customThe reaction mixture is evaporated
  3. dissolutionThe oily residue is dissolved in 400 parts of water
  4. extractionThe sticky product is extracted with 1,1'-oxybisethane
  5. washThe extract is washed twice with water
  6. customdried
  7. customevaporated
  8. customThe oily residue is triturated three times in petroleumether
  9. filtrationThe solid product is filtered off
  10. customrecrystallized from 50 parts of glacial acetic acid
  11. washThe product is washed with petroleumether
  12. customdried
  13. dissolutiondissolved in 80 parts of 1,1'-oxybisethane
  14. stirringThe solution is stirred with activated charcoal
  15. filtrationfiltered
  16. customthe filtrate is evaporated
  17. customon triturating in 2-propanol
  18. filtrationThe solid is filtered off
  19. customdried

Sources & evidence

ORD record
ord-ac3fda0daa6744ef8cacb3ee5f3b7b1b
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

Loading…