Bromomethyl 4-methoxyphenyl ketone → 4-[4-Amino-5-(4-methoxy-benzoyl)-thiazol-2-ylamino]-benzoic Acid Methyl Ester

HRID 413731Notes

Reaction equation

HRID 413731 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]=[S:13])=[CH:7][CH:6]=1)=[O:4].[N:14]#[C:15][NH2:16].CC(C)([O-])C.[K+].Br[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:26]>C(#N)C.C(O)(C)(C)C.O>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[S:13][C:24]([C:25](=[O:26])[C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)=[C:15]([NH2:16])[N:14]=2)=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 9864CyanamideHCID 1380024-Methoxycarbonylphenyl isothiocyanateHCID 23665647Potassium tert-butoxide

Product 1

HCID 205905724-[4-Amino-5-(4-methoxy-benzoyl)-thiazol-2-ylamino]-benzoic Acid Methyl EsterYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

To a mixture of 4-methoxycarbonylphenyl isothiocyanate (82 mg, 0.5 mmol) and cyanamide (23 mg, 0.55 mmol) in acetonitrile (5 mL), a solution of potassium tert-butoxide (61 mg, 0.55 mmol) in tert-butanol (5 mL) was added. After 30 minutes at ambient temperature, 2-bromo-4′-methoxy-acetophenone (115 mg, 0.5 mmol) was added. After 2 hours at ambient temperature, the reaction mixture was diluted with water (50 mL). The product was collected by filtration, rinsed with water and ethyl ether, and dried under vacuum to furnish a yellow solid, 172 mg (90% yield).

Workup

  1. waitAfter 2 hours at ambient temperature
  2. filtrationThe product was collected by filtration
  3. washrinsed with water and ethyl ether
  4. customdried under vacuum
  5. customto furnish a yellow solid, 172 mg (90% yield)

Sources & evidence

ORD record
ord-6593ffcf737147e6a98eae6e86443688
Source dataset
uspto-grants-2003_05
Patent number
US06569878B1

Reaction notes

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