4-Chloroaniline → Benzothiazol-2-yl-(4-chloro-phenyl)-amine

HRID 1593517Notes

Reaction equation

HRID 1593517 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>C(O)(=O)C.O>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:16][C:15]1[CH:17]=[CH:18][C:12]([Cl:11])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 78124-ChloroanilineHCID 119872-Chlorobenzothiazole

Product 1

HCID 234666Benzothiazol-2-yl-(4-chloro-phenyl)-amineYield 54%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1.7 g (10 mmol) 2-chloro-1,3-benzothiazole and 2.6 g (10 mmol) 4-chloroaniline in 20 ml acetic acid was heated to 110° C. for 3 h. The reaction mixtures was diluted with 200 ml water and the resulting mixture was extracted with 3×150 ml ethyl acetate. The combined organic phases were washed with 2×100 ml water, dried with MgSO4, filtered and evaporated to dryness. The residue was recrystallysed from a mixture of hexane/ethyl acetate to yield 1.4 g (54%) of the title compound.

Workup

  1. customThe reaction mixtures
  2. extractionthe resulting mixture was extracted with 3×150 ml ethyl acetate
  3. washThe combined organic phases were washed with 2×100 ml water
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. additionThe residue was recrystallysed from a mixture of hexane/ethyl acetate

Sources & evidence

ORD record
ord-84dc7843b7f8417888c210ebb6c92fcc
Source dataset
uspto-grants-2007_11
Patent number
US07297707B2

Reaction notes

Loading…