2-Chloro-N,N-dimethylethylamine → HCID 70490372, compound

HRID 1154511Notes

Reaction equation

HRID 1154511 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[C:10]1[C:15](=O)[NH:14][C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[S:11]1.[OH-].[Na+].[CH3:23][N:24]([CH2:26][CH2:27]Cl)[CH3:25]>C(C(C)=O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[C:10]1[CH2:15][N:14]([CH2:27][CH2:26][N:24]([CH3:25])[CH3:23])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[S:11]1

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 14798Sodium HydroxideHCID 542496372-[(2,4-Dichlorophenyl)methylidene]-2H-1,4-benzothiazin-3(4H)-one

Product 1

HCID 70490372HCID 70490372, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(2,4-Dichlorophenylmethylidene)-2H-1,4-benzothiazine-3(4H)-one (3.0 g) in methyl ethyl ketone (10 ml) was treated with sodium hydroxide (0.98 g) at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature and added with dimethylaminoethyl chloride (1.7 g), refluxed for 3 hours and cooled to 30° C. The organic layer was washed with 20 ml of water two times, dried and evaporated under reduced pressure. The residue was dissolved in 20 ml of isopropyl alcohol and added with 0.9 ml of conc. HCl. The resulted precipitates were filtered and recrystallized from 30 ml of isopropyl alcohol to give 2-(2,4-Dichlorophenylmethylidene)-4-(2-dimethylaminoethyl)-2H-1,4-benzothiazine hydrochloride as yellow crystals. m.p. 238° to 242° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperaturecooled to 30° C
  3. washThe organic layer was washed with 20 ml of water two times
  4. customdried
  5. customevaporated under reduced pressure
  6. dissolutionThe residue was dissolved in 20 ml of isopropyl alcohol
  7. additionadded with 0.9 ml of conc. HCl
  8. customThe resulted precipitates
  9. filtrationwere filtered
  10. customrecrystallized from 30 ml of isopropyl alcohol

Sources & evidence

ORD record
ord-3d912fb0f9144e58a7e18e4a07edb791
Source dataset
uspto-grants-1984_12
Patent number
US04490292

Reaction notes

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