4-(4-Methylphenyl)-1,3-thiazole-2-carboxylic acid → HCID 178423924, compound

HRID 1708946Notes

Reaction equation

HRID 1708946 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]([OH:15])=O)[S:11][CH:12]=2)=[CH:4][CH:3]=1.[NH2:16][C:17]1[NH:21][N:20]=[N:19][N:18]=1>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]([NH:16][C:17]3[NH:21][N:20]=[N:19][N:18]=3)=[O:15])[S:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 147727214-(4-Methylphenyl)-1,3-thiazole-2-carboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178423924HCID 178423924, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-(4-methylphenyl)-2-thiazolecarboxylic acid (300 mg, 1.37 mmol) and N,N -carbonyl diimidazole (CDI) (444.3 mg, 2.74 mmol) dissolved in dry DMF (5 ml) was stirred at room temperature for 1 hour. Under the same conditions, a solution of 5-aminotetrazole (139.5 mg, 1.64 mmol) in dry DMF was added thereto, and the resulting mixture was allowed to react at 85° C. for 2 hours. After removing of the solvent from the reaction mixture by distillation, the residue was treated with water and acidified with 1N-HCl to pH 2. The deposited solids were filtered with suction, washed with water and recrystallized from methanol-THF-water to give 258 mg (yield 66%) of 4-(4-methylphenyl)-N-(1H-tetrazole-5-yl)-2-thiazolecarboxamide as pale yellow crystals, m.p. 276°-278° C.

Workup

  1. customto react at 85° C. for 2 hours
  2. customAfter removing of the solvent from the reaction mixture by distillation
  3. additionthe residue was treated with water
  4. filtrationThe deposited solids were filtered with suction
  5. washwashed with water
  6. customrecrystallized from methanol-THF-water

Sources & evidence

ORD record
ord-db49f71db1914d0b9e62c24a9be365d2
Source dataset
uspto-grants-1990_08
Patent number
US04946855

Reaction notes

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