Water → Benzamide

HRID 2102805Notes

Reaction equation

HRID 2102805 reaction equation
[NH2:1]C1SC2C=C([N+]([O-])=O)C=CC=2N=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>N1C=CC=CC=1>[C:14]([NH2:1])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chloride2×HCID 227042-Amino-6-nitrobenzothiazole

Product 1

HCID 2331BenzamideYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 2-amino-6-nitrobenzothiazole (Sigma Aldrich, 2.93 g, 15 mmol) in pyridine (20 mL), benzoyl chloride (1.74 mL, 15 mmol) was added. After stirring over-night at r.t., additional benzoyl chloride (1.74 mL, 15 mmol) was added and the mixture was stirred at 60° C. After completion of the reaction, the mixture was poured into water (250 mL) and stirred overnight at r.t. Separation of the resulting precipitate yielded N-6-nitrobenzotihiazol-2-yl)benzamide (3.87 g, 12.9 mmol, 86%) as a yellow solid. LC/ESI-MS: m/z=300 [M+H]+; m/z=298 [M−H]−; Rt=3.93 min.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 60° C
  3. customAfter completion of the reaction
  4. stirringstirred overnight at r.t
  5. customSeparation of the resulting precipitate

Sources & evidence

ORD record
ord-c11eb08136cd4546907c236f1cce103d
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Reaction notes

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