Water → N-[4-(1,3-benzothiazol-2-yl)phenyl]benzamide

HRID 1636565Notes

Reaction equation

HRID 1636565 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>N1C=CC=CC=1>[C:17]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 2344752-(4-Aminophenyl)benzothiazole

Product 1

HCID 720780N-[4-(1,3-benzothiazol-2-yl)phenyl]benzamideYield 82.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-(4'-aminophenyl)benzothiazole (0.3 g, 1.32 mmol) and benzoyl chloride (0.3 ml) in pyridine (8 ml) was stirred at reflux for 2 hours, then cooled and poured into water (100 ml). The precipitate formed was filtered off, washed with water and dissolved in hot dichloromethane (12 ml). The resulting solution was cooled in an ice-bath and the solid was filtered off. The filtrate was evaporated and the residue was recrystallised from dichloromethane-methanol to give a white powder (0.36 g, 82.2%), m.p. 227.1-228.5° C.

Workup

  1. temperatureat reflux for 2 hours
  2. temperaturecooled
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. washwashed with water
  6. dissolutiondissolved in hot dichloromethane (12 ml)
  7. temperatureThe resulting solution was cooled in an ice-bath
  8. filtrationthe solid was filtered off
  9. customThe filtrate was evaporated
  10. customthe residue was recrystallised from dichloromethane-methanol

Sources & evidence

ORD record
ord-0af5bb72ee8c4805a786caac2d3f543a
Source dataset
uspto-grants-2000_03
Patent number
US06034246

Reaction notes

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