Phosphorus oxychloride → HCID 86746999, compound

HRID 1588604Notes

Reaction equation

HRID 1588604 reaction equation
[C:1]([O:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][N:14]([CH3:17])[C:13]1=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.P(Cl)(Cl)(Cl)=O.[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41]>C1C=CC=CC=1.CO>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41].[C:1]([O:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][N:14]([CH3:17])[C:13]1=[N:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 7357562-MorpholinoanilineHCID 15746397HCID 15746397, compound

Product 1

HCID 86746999HCID 86746999, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 887MethanolSolvent

Procedure

In a similar manner to that described in Example 133, 1-(2-benzoyloxyethyl)-3-methyl-2-imidazolidinone (8.8 g) in benzene (30 ml) was reacted with 4-(2-aminophenyl)morpholine (5.2 g) in benzene (20 ml) in the presence of phosphorus oxychloride (3.3 ml) for 35 hours at 80°-85° C. to yield an oil. The oil was dissolved in methanol (10 ml) and treated with fumaric acid (1.8 g). The solvent was removed by evaporation and the residue washed with ether and then dissolved in water. The aqueous solution was basified with aqueous sodium carbonate solution to pH 9-10 and extracted with ether to yield an oil which was purified by chromatography on an alumina column using dichloromethane as eluant. The purified base (0.8 g) in methanol (10 ml) was treated with fumaric acid (0.23 g) to give 4-((2-[1-(2-benzoyloxyethyl)-3-methyl-2-imidazolidinylideneamino]phenyl))morpholine monofumarate (m.p. 132°-133° C.) which was recrystallised from 1:2 mixture of methanol and ether.

Workup

  1. customto yield an oil
  2. customThe solvent was removed by evaporation
  3. washthe residue washed with ether
  4. dissolutiondissolved in water
  5. extractionextracted with ether
  6. customto yield an oil which
  7. customwas purified by chromatography on an alumina column
  8. additionThe purified base (0.8 g) in methanol (10 ml) was treated with fumaric acid (0.23 g)

Sources & evidence

ORD record
ord-d2c8aeb57b154d5597c10484494a93f6
Source dataset
uspto-grants-1993_06
Patent number
US05223498

Reaction notes

Loading…