Hydrochloric Acid → N-(4-Methoxy-7-phenyl-benzothiazol-2-yl)-benzamide

HRID 2250662Notes

Reaction equation

HRID 2250662 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:8]=[C:7]([O:17][CH3:18])[C:5]=2[N:6]=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>N1C=CC=CC=1>[CH3:18][O:17][C:7]1[C:5]2[N:6]=[C:2]([NH:1][C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:3][C:4]=2[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 222830262-Amino-4-methoxy-7-phenyl-benzothiazole

Product 1

HCID 22283378N-(4-Methoxy-7-phenyl-benzothiazol-2-yl)-benzamideYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-amino-4-methoxy-7-phenyl-benzothiazole (100 mg, 0.4 mmol) in pyridine (2 ml) was added benzoyl chloride (55 mg, 0.4 mmol) and the mixture stirred overnight at 20° C. To this mixture 2N HCl to pH 1 (20 ml) was added then the mixture was extracted twice with EtOAc (20 ml), washed with saturated NaHCO3 solution, dried with Na2SO4 and the solvent evaporated. The crude product was then chromatographed over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2/MeOH (98:2), the product fractions were pooled and the solvent evaporated, to afford the title compound as a white solid (97 mg, 69% yield), MS: m/e=360 (M+).

Workup

  1. extractionthe mixture was extracted twice with EtOAc (20 ml)
  2. washwashed with saturated NaHCO3 solution
  3. dry with materialdried with Na2SO4
  4. customthe solvent evaporated
  5. customThe crude product was then chromatographed over SiO2 (Merck 230-400 mesh)
  6. washeluting with CH2Cl2/MeOH (98:2)
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-791258faf6f049f1bfafe1a6f2081175
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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