Methylthiourea → 4-[2-(Methylamino)-1,3-thiazol-4-yl]benzoic acid

HRID 606600Notes

Reaction equation

HRID 606600 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.[CH3:14][NH:15][C:16]([NH2:18])=[S:17]>C(O)C>[CH3:14][NH:15][C:16]1[S:17][CH:2]=[C:3]([C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)[N:18]=1

Participants

4

Reactant 2

HCID 2723704MethylthioureaHCID 27568364-(2-bromoacetyl)benzoic Acid

Product 1

HCID 598073534-[2-(Methylamino)-1,3-thiazol-4-yl]benzoic acidYield 103.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To 25 ml of ethanol were added 4-(2-bromoacetyl)benzoic acid (486 mg, 2 mmole) and N-methyl thiourea (180 mg, 2 mmole). The reaction mixture was refluxed for 3 hr and the TLC showed the disappearing of the starting materials and the formation of a fluorescent product. The reaction was cooled on ice. The product was collected on filtration and washed with ethanol pre-cooled to 0° C. twice (2×3 ml), followed by diethyl ether. After drying, 486 mg product was obtained. 1H NMR (DMSO-d6, 400 MHz) δ 7.97 (2H, d), 7.89 (2H, d), 7.32 (1H, s), 2.96 (3H, s).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hr
  2. temperatureThe reaction was cooled on ice
  3. filtrationThe product was collected on filtration
  4. washwashed with ethanol
  5. customAfter drying

Sources & evidence

ORD record
ord-91da2aa0c49f41bc8c5892fbe50f0692
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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