5-Chloro-2,4-dimethoxyaniline → N-(5-Chloro-2,4-dimethoxyphenyl)-4H-3,1-benzothiazin-2-amine

HRID 1414709Notes

Reaction equation

HRID 1414709 reaction equation
CS[C:3]1[S:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]=1.[Cl:13][C:14]1[C:15]([O:23][CH3:24])=[CH:16][C:17]([O:21][CH3:22])=[C:18]([CH:20]=1)[NH2:19]>C(O)CCC>[Cl:13][C:14]1[C:15]([O:23][CH3:24])=[CH:16][C:17]([O:21][CH3:22])=[C:18]([CH:20]=1)[NH:19][C:3]1[S:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 668075-Chloro-2,4-dimethoxyanilineHCID 214848902-(Methylsulfanyl)-4H-3,1-benzothiazine

Product 1

HCID 21484882N-(5-Chloro-2,4-dimethoxyphenyl)-4H-3,1-benzothiazin-2-amineYield 43.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-methylthio-4H-3,1-benzothiazine (48.8 g, 0.25 mole) and 5-chloro-2,4-dimethoxyaniline (46.8 g, 0.25 mole) in n-butanol (200 ml) was refluxed overnight. After cooling in ice, the solid was collected by filtration and recrystallized from ethanol to give 36 g (43.4%) of product. Recrystallization from ethanol gave an analytical sample, m.p. 157°-158°.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling in ice
  3. filtrationthe solid was collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8559823372844f3ba41e18373ab28585
Source dataset
uspto-grants-1977_01
Patent number
US04002620

Reaction notes

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