Phosphorus oxychloride → HCID 86746999, compound

HRID 1492197Notes

Reaction equation

HRID 1492197 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-imidazolidone (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 a 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-79faa25e0c9541f4b45c1c564af9b342
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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