Sodium Bicarbonate → Benzamide

HRID 2102818Notes

Reaction equation

HRID 2102818 reaction equation
NC1C=CC2N=C([NH:9][C:10](=[O:17])[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)SC=2C=1.ClC1C2C(=CC(OC)=C(OC)C=2)N=CN=1.C(=O)([O-])O.[Na+]>C(O)CO.[Cl-].[Na+].O>[C:10]([NH2:9])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 810331N-(6-amino-1,3-benzothiazol-2-yl)benzamideHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

N-[6-6,7-Dimethoxyquinazolin-4-ylamino)benzothiazol-2-yl]benzamide was prepared by heating a mixture of N-(6-aminobenzothiazol-2-yl)benzamide (IM 2, 30 mg, 0.111 mmol) and 4-chloro-6,7-dimethoxyquinazoline (Fluorochem, 25 mg, 0.111 mmol) in ethylene glycol (0.7 mL) to 100° C. for 2 h. Brine (25 mL) and saturated sodium hydrogencarbonate solution (25 mL) were added and the product was extracted with chloroform (3×40 mL). After drying out Na2SO4, the solvent was removed and the residue was purified by pTLC (petroleum ether:dichloromethane:methanol=12:14:3) to yield a yellow solid (19 mg, 41 μmol, 37%). LC/ESI-MS: m/z 458 [M+H]+; m/z=456 [M−H]−; Rt=2.88 min.

Workup

  1. temperatureby heating
  2. extractionthe product was extracted with chloroform (3×40 mL)
  3. dry with materialAfter drying out Na2SO4
  4. customthe solvent was removed
  5. customthe residue was purified by pTLC (petroleum ether:dichloromethane:methanol=12:14:3)

Sources & evidence

ORD record
ord-51e3086cfc2f4f228c92f08fa9a17ca2
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Reaction notes

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