3-Chloroaniline → 6-Chloro-N-(3-chlorophenyl)-4H-3,1-benzothiazin-2-amine

HRID 1414713Notes

Reaction equation

HRID 1414713 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[C:9](SC)[S:8][CH2:7][C:6]=2[CH:13]=1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18]>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[C:9]([NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[C:15]([Cl:14])[CH:16]=3)[S:8][CH2:7][C:6]=2[CH:13]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 21484887HCID 21484887, compound

Product 1

HCID 214848856-Chloro-N-(3-chlorophenyl)-4H-3,1-benzothiazin-2-amineYield 52%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 6-chloro-2-methylthio-4H-3,1-benzothiazine (69 g, 0.30 mole) and 3-chloroaniline (38.2 g, 0.30 mole) in n-butanol (250 ml) was refluxed overnight. After cooling in ice, the solid was collected by filtration and recrystallized from ethanol-water mixture to give 48 g (52%) of title product, m.p. 174°-175°.

Workup

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

Sources & evidence

ORD record
ord-9e45bbc3043d4e4dbf230c8b4b2ec94a
Source dataset
uspto-grants-1977_01
Patent number
US04002620

Reaction notes

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