Toluene → HCID 21403315, compound

HRID 973035Notes

Reaction equation

HRID 973035 reaction equation
[NH:1]=[C:2]([C:9]1[C:10](=[O:23])[N:11]([CH3:22])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:13][C:14]=1[OH:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1.[C:38](Cl)(Cl)=[O:39]>C1C=CC=CC=1>[CH3:22][N:11]1[C:12]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:13][C:14]2[O:15][C:38](=[O:39])[N:1]=[C:2]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:9]=2[C:10]1=[O:23]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 1354009813-(alpha-Iminobenzyl)-4-hydroxy-6-phenyl-1-methyl-2(1H)-pyridinone

Product 1

HCID 21403315HCID 21403315, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 10 g. (0.0348 mole) of 3-(α-iminobenzyl)-4-hydroxy-6-phenyl-1-methyl-2(1H)-pyridone and 7.3 g. (0.0724 mole) triethylamine in 200 ml. toluene is treated portionwise with 30 ml. (27.8 g., 0.0348 mole) of a 12.5% solution of phosgene in benzene. The resulting mixture becomes warm and the solids are separated out. The mixture is then stirred at room temperture for 18 hours and then poured onto water and filtered. The solids are washed with toluene. The toluene and water filtrate is separated and the toluene dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The resulting solid is recrystallized with hot toluene to give 6-methyl-4,7-diphenyl-2H-pyrido[3,4-e]-1,3-oxazine-2,5-dione, m.p. 178°-179° C.

Workup

  1. additionA mixture of 10 g
  2. temperatureThe resulting mixture becomes warm
  3. customthe solids are separated out
  4. additionpoured onto water
  5. filtrationfiltered
  6. washThe solids are washed with toluene
  7. customThe toluene and water filtrate is separated
  8. dry with materialthe toluene dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe resulting solid is recrystallized with hot toluene

Sources & evidence

ORD record
ord-5f8f061980004ca08e1e59267705c581
Source dataset
uspto-grants-1977_10
Patent number
US04054653

Reaction notes

Loading…