4-(2-bromoacetyl)benzoic Acid → 4-[2-(Pyridin-3-ylamino)-thiazol-4-yl]-benzoic acid

HRID 1016470Notes

Reaction equation

HRID 1016470 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)=O.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([NH2:23])=[S:22])[CH:15]=1>C(O)C>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]2[S:22][CH:2]=[C:3]([C:5]3[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=3)[N:23]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 27568364-(2-bromoacetyl)benzoic AcidHCID 27605153-Pyridylthiourea

Product 1

HCID 181865234-[2-(Pyridin-3-ylamino)-thiazol-4-yl]-benzoic acidYield 739.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-bromoacetylbenzoic acid (2.2 g, 10 mmol) in ethanol (50 mL) was treated with pyrid-3-ylthiourea (1.53 g, 1 mmol) and the mixture was refluxed for 3 hr. Solids were collected by filteration, washed with ether and dried to provide 4-(2-pyrid-3-ylaminothiazol-4-yl)benzoic acid (2.2 g, 74% yield). LC-MS: FAB LC-MS. 298.2 (M+H+).

Workup

  1. temperaturethe mixture was refluxed for 3 hr
  2. customSolids were collected by filteration
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-a4170d55ba224bf2b290b51ae41675a6
Source dataset
uspto-grants-2002_11
Patent number
US06476026B1

Reaction notes

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