Acetone → 1-[3-(dimethylamino)-propyl]-3-(3-trifluoromethylphenyl)-1H-naphtho[2,1-b][1,4]-thiazin-2(3H)-one

HRID 1198447Notes

Reaction equation

HRID 1198447 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:9]2[S:14][C:13]3[CH:15]=[CH:16][C:17]4[C:22]([C:12]=3[NH:11][C:10]2=[O:23])=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:33][N:34]([CH3:39])[CH2:35][CH2:36][CH2:37]Cl.CC(C)=O>O>[CH3:33][N:34]([CH3:39])[CH2:35][CH2:36][CH2:37][N:11]1[C:10](=[O:23])[CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:24])[F:25])[CH:4]=2)[S:14][C:13]2[CH:15]=[CH:16][C:17]3[C:22]([C:12]1=2)=[CH:21][CH:20]=[CH:19][CH:18]=3

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 189844253-(3-trifluoromethylphenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one

Product 1

HCID 189844281-[3-(dimethylamino)-propyl]-3-(3-trifluoromethylphenyl)-1H-naphtho[2,1-b][1,4]-thiazin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(3-trifluoromethylphenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (18.0 g), potassium carbonate (24.2 g), 3-(dimethylamino)propyl chloride hydrochloride (9.5 g), acetone (400 ml) and water (4 ml) is refluxed for 48 hours. The insoluble materials are filtered off and acetone is distilled off, and to the residue are added ethanol (200 ml) and 10% hydrochloric acid (100 ml), and the mixture is refluxed for one hour. After ethanol is distilled off and the insoluble materials are filtered off, the resulting mixture is made alkaline with sodium hydrogen carbonate and extracted with ethyl acetate. The extract is distilled to remove the solvent to give 1-[3-(dimethylamino)propyl]-3-(3-trifluoromethylphenyl)-1H-naphtho[2,1-b][1,4]-thiazin-2(3H)-one as oil.

Workup

  1. temperatureis refluxed for 48 hours
  2. filtrationThe insoluble materials are filtered off
  3. distillationacetone is distilled off
  4. additionto the residue are added ethanol (200 ml) and 10% hydrochloric acid (100 ml)
  5. temperaturethe mixture is refluxed for one hour
  6. distillationAfter ethanol is distilled off
  7. filtrationthe insoluble materials are filtered off
  8. extractionextracted with ethyl acetate
  9. distillationThe extract is distilled
  10. customto remove the solvent

Sources & evidence

ORD record
ord-7682244b532b4f6d91530b12275275c9
Source dataset
uspto-grants-1994_01
Patent number
US05281592

Reaction notes

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