3,4-Dichloroaniline → N-(3,4-Dichlorophenyl)-4H-3,1-benzothiazin-2-amine

HRID 1414710Notes

Reaction equation

HRID 1414710 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[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[Cl:21])[NH2:17]>C(O)CCC>[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[Cl:21])[NH:17][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 72573,4-DichloroanilineHCID 214848902-(Methylsulfanyl)-4H-3,1-benzothiazine

Product 1

HCID 21484883N-(3,4-Dichlorophenyl)-4H-3,1-benzothiazin-2-amineYield 43.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-methylthio-4H-3,1-benzothiazine (39 g, 0.20 mole) and 3,4-dichloroaniline (32.4 g, 0.20 mole) in n-butanol (150 ml) was refluxed overnight. After cooling in ice, the solid was collected by filtration and recrystallized from ethanol to give 27 g (43.8%) of product. Recrystallization from ethanol gave analytical sample m.p. 207°-208°.

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-e120507017f14f668aaf8ce8552ac46b
Source dataset
uspto-grants-1977_01
Patent number
US04002620

Reaction notes

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