Water → N-Benzothiazol-2-yl-benzamide

HRID 925150Notes

Reaction equation

HRID 925150 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>N1C=CC=CC=1>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:1][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8706Benzo(d)thiazol-2-amine

Product 1

HCID 689669N-Benzothiazol-2-yl-benzamideYield 64.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
3 °C

Procedure

In a 100 ml three-necked flask equipped with magnetic stirrer, thermometer, dropping funnel and nitrogen inlet, 5.34 g (35.6 mmol) of 2-amino-benzothiazole are dissolved in 50 ml of pyridine and cooled to 3° C. using an ice bath. 5.0 g of benzoylchloride (35.6 mmol) are added dropwise within 20 minutes, keeping the temperature within the mixture below 5° C. Stirring is continued for another 15 minutes, then the mixture is poured on 500 ml of water. The white suspension is stirred for 1 hour, filtered, the white residue is washed 3 times with 100 ml of water, respectively, and dried over night at 50° C. and 30 mbar. 7.5 g crude product obtained are purified by flash-chromatography using hexane/ethylacetate 3:1 (v/v), yielding 5.8 g of the title product.

Workup

  1. customIn a 100 ml three-necked flask equipped with magnetic stirrer
  2. customwithin the mixture below 5° C
  3. stirringThe white suspension is stirred for 1 hour
  4. filtrationfiltered
  5. washthe white residue is washed 3 times with 100 ml of water
  6. customrespectively, and dried over night at 50° C.
  7. custom7.5 g crude product obtained
  8. customare purified by flash-chromatography

Sources & evidence

ORD record
ord-99f3607575db443492267e9bf7e9402e
Source dataset
uspto-grants-2016_03
Patent number
US09284278B2

Reaction notes

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