Diethyl Ether → N-[4-chloro-3-[(4-morpholinylimino)methyl]phenyl]-2-methyl-3-furancarboxamide

HRID 1416551Notes

Reaction equation

HRID 1416551 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:15]=[CH:14][O:13][C:12]=2[CH3:16])=[O:10])=[CH:4][C:3]=1[CH:17]=O.[NH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(Cl)Cl.CCOCC>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:15]=[CH:14][O:13][C:12]=2[CH3:16])=[O:10])=[CH:4][C:3]=1[CH:17]=[N:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 20315N-AminomorpholineHCID 54027287N-(4-chloro-3-formylphenyl)-2-methyl-3-furancarboxamide

Product 1

HCID 67563349N-[4-chloro-3-[(4-morpholinylimino)methyl]phenyl]-2-methyl-3-furancarboxamideYield 87.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a chilled suspension of N-(4-chloro-3-formylphenyl)-2-methyl-3-furancarboxamide (2.0 g) in methanol (30 ml) was added 4-aminomorpholine (0.8 g). The resultant reaction mixture was stirred overnight. TLC analysis (methlyenechloride:ether, 5:1) of the reaction mixture showed a new spot and traces of substrate. The reaction mixture was stirred for another hour at 30° C. and then the reaction mixture was poured into water and extracted into ether/ethyl acetate. The extract was washed with water, dried (MgSO4), filtered, and evaporated to leave a solid. The solid was then covered with ether/ligroin and stirred for several hours and then collected on a filter to give 2.3 g of N-[4-chloro-3-[(4-morpholinylimino)methyl]phenyl]-2-methyl-3-furancarboxamide as an off-white solid, mp 121-123° C.

Workup

  1. customThe resultant reaction mixture
  2. stirringThe reaction mixture was stirred for another hour at 30° C.
  3. extractionextracted into ether/ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a solid
  9. stirringstirred for several hours
  10. customcollected on
  11. filtrationa filter

Sources & evidence

ORD record
ord-0bc5b1670d0a453f9856276ec7c10b88
Source dataset
uspto-grants-1999_06
Patent number
US05914351

Reaction notes

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