Water → 3-(4-chlorophenyl)-1-(3-chloropropyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one

HRID 5835Notes

Reaction equation

HRID 5835 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:13][C:12]3[CH:14]=[CH:15][C:16]4[C:21]([C:11]=3[NH:10][C:9]2=[O:22])=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:26][CH2:27][CH2:28][Cl:29].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:13][C:12]3[CH:14]=[CH:15][C:16]4[C:21]([C:11]=3[N:10]([CH2:26][CH2:27][CH2:28][Cl:29])[C:9]2=[O:22])=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 189844403-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one

Product 1

HCID 540273853-(4-chlorophenyl)-1-(3-chloropropyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-oneYield 65.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-(4-chlorophenyl)-1H-naphtho-[2,1-b][1,4]thiazin-2(3H)-one (10.0 g) and 96% sodium hydroxide (1.96 g) in dimethylsulfoxide (150 ml) is added 1-bromo-3-chloropropane (6.78 g) under ice cooling, and the mixture is stirred at room temperature overnight. The reaction mixture is poured into water, and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed and distilled to remove the solvent. The residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1) and further is recrystallized from methanol to give 3-(4-chlorophenyl)-1-(3-chloropropyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (8.04 g). M.p. 110°-112.5° C.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe ethyl acetate layer is washed
  3. distillationdistilled
  4. customto remove the solvent
  5. customThe residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1)
  6. customfurther is recrystallized from methanol

Sources & evidence

ORD record
ord-b63569a6c9d54dc68412742b3466264e
Source dataset
uspto-grants-1993_09
Patent number
US05246929

Reaction notes

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