Thiobenzamide → 5-Ethyl-2-phenyl-1,3-thiazole-4-carboxylic acid

HRID 2300592Notes

Reaction equation

HRID 2300592 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:11]([CH2:19][CH3:20])[C:12](=O)[C:13]([O:15]CC)=[O:14]>C1(C)C=CC=CC=1>[CH2:19]([C:11]1[S:8][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:9][C:12]=1[C:13]([OH:15])=[O:14])[CH3:20]

Participants

4

Reactant 2

HCID 683563ThiobenzamideHCID 14740334Ethyl 3-bromo-2-oxopentanoate

Product 1

HCID 138353095-Ethyl-2-phenyl-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Intermediate 2C was prepared as described above for the preparation of intermediate 2B from 4.61 g of thiobenzamide, 5.0 g of ethyl 3-bromo-2-oxo-pentanoate, and 14 mL of toluene. Solids were collected and washed with cold water after cooling of the NaOH solution. Heating these solids with citric acid as described followed by cooling and isolation of the resulting solids gave 3.74 g (72% yield) of intermediate 2C; 1H NMR (CDCl3, 300 MHz) δ7913-7.91 (m, 2H), 7.51-7.50 (m, 3H), 3.39 (q, 2H, J=7.8), 1.42 (t, 3H, J=7.8); low resolution MS (ES+)m/e 233.81 (MH+).

Workup

  1. customSolids were collected
  2. washwashed with cold water
  3. temperatureafter cooling of the NaOH solution
  4. temperatureHeating these solids with citric acid
  5. temperatureby cooling

Sources & evidence

ORD record
ord-6d6aae3e4bf6446399b3a3eab075c8cb
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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