Phosphorus oxychloride → HCID 59609612, compound

HRID 1660689Notes

Reaction equation

HRID 1660689 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]1([CH3:28])[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[C:7]=1[N:14]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[S:21][C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2.CN([CH:37]=[O:38])C1C=CC=CC=1.C([O-])(=O)C.[Na+]>ClC1C=CC=CC=1Cl.O>[C:6]1([CH3:28])[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[C:7]=1[N:14]1[C:27]2[CH:26]=[CH:25][C:24]([CH:37]=[O:38])=[CH:23][C:22]=2[S:21][C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 517045Sodium AcetateHCID 59572574HCID 59572574, compound

Product 1

HCID 59609612HCID 59609612, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
70 °C

Procedure

3.66 g (23.6 mmol) of 99% phosphorus oxychloride were added dropwise at 20° C. with stirring and ice cooling to a solution of 5.00 g (15.8 mmol) of 10-mesitylphenothiazine and 3.23 g (23.6 mmol) of 99% N-methylformanilide in 5 ml of o-dichlorobenzene within 15 min. After stirring at 20° C. for 30 min, the reaction solution was heated to 70° C. and kept at this temperature for 4 hours. The reaction solution was admixed with a solution of 16 g of sodium acetate in 35 ml of water within 5 min. After stirring at 70° C. for 1 hour, N-methylformanilide and o-dichlorobenzene were removed with a steam distillation. 250 ml of methylene chloride were added to the distillation bottoms. The organic phase was removed and filtered through silica gel. The filtrate was concentrated and dried at 40° C. under reduced pressure. 5.05 g (93% of theory) of analytically pure greenish powder having a melting point of 136-140° C. were obtained.

Workup

  1. stirringAfter stirring at 20° C. for 30 min
  2. stirringAfter stirring at 70° C. for 1 hour
  3. customN-methylformanilide and o-dichlorobenzene were removed with a steam distillation
  4. addition250 ml of methylene chloride were added to the distillation bottoms
  5. customThe organic phase was removed
  6. filtrationfiltered through silica gel
  7. concentrationThe filtrate was concentrated
  8. customdried at 40° C. under reduced pressure
  9. customwere obtained

Sources & evidence

ORD record
ord-1b749d67acf84475b4e75548439ac5cc
Source dataset
uspto-grants-2011_10
Patent number
US08029919B2

Reaction notes

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