2-(2-Methoxyphenyl)-1,3-thiazole-4-carboxylic acid → HCID 178489364, compound

HRID 1638319Notes

Reaction equation

HRID 1638319 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1.[NH2:17][C:18]1[NH:22][N:21]=[N:20][N:19]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]([NH:17][C:18]2[NH:22][N:21]=[N:20][N:19]=2)=[O:16])[N:13]=1

Participants

4

Reactant 2

HCID 156230682-(2-Methoxyphenyl)-1,3-thiazole-4-carboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178489364HCID 178489364, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-(2-methoxyphenyl)-4-thiazolecarboxylic acid (250 mg) and N,N'-carbonyldimidazole (CDI, 207 mg) in dry DMF (2.5 ml) was allowed to react with stirring at room temperature for 1 hour. Then a solution of 5-aminotetrazole (109 mg) in dry DMF (1.5 ml) was added dropwise thereto and allowed to react at 70° C. for 2 hours. The solvent was removed from the mixture, and the residue was treated with water and acidified with 2N-HCl. The produced solids were filtered, washed with water, treated with stirring with ether, filtered again and dried to give white solids of the desired 2-(2-methoxyphenyl)-N-(1H-tetrazole-5-yl)-4-thiazolecarboxamide (255 mg, 79%).

Workup

  1. customto react
  2. customto react at 70° C. for 2 hours
  3. customThe solvent was removed from the mixture
  4. additionthe residue was treated with water
  5. filtrationThe produced solids were filtered
  6. washwashed with water
  7. additiontreated
  8. stirringwith stirring with ether
  9. filtrationfiltered again
  10. customdried

Sources & evidence

ORD record
ord-31e2c47a2c61427ebbf239b329887990
Source dataset
uspto-grants-1989_11
Patent number
US04879295

Reaction notes

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