1,1'-Carbonyldiimidazole → HCID 178423976, compound

HRID 1638324Notes

Reaction equation

HRID 1638324 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[S:8][C:9]([CH3:15])=[C:10]([C:12](O)=[O:13])[N:11]=2)=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:28][C:29]1[NH:33][N:32]=[N:31][N:30]=1>CN(C=O)C>[CH3:1][C:2]1[S:6][C:5]([C:7]2[S:8][C:9]([CH3:15])=[C:10]([C:12]([NH:28][C:29]3[NH:33][N:32]=[N:31][N:30]=3)=[O:13])[N:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 156230735-Methyl-2-(5-methyl-2-thienyl)-4-thiazolecarboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178423976HCID 178423976, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 2-(5-methyl-2-thienyl)-5-methyl-4-thiazolecarboxylic acid (300 mg) and CDI (304.9 mg) in dry DMF (3 ml) was allowed to react at room temperature for 1 hour. Then a solution of 5-aminotetrazole (128 mg) in dry DMF (2 ml) was added dropwise and the mixture was heated at 70° C. for 3 hours. The solvent was removed from the reaction mixture, and the residue was treated with water and acidified with 2N-HCl under ice-cooling. The produced solids were filtered with suction, washed sufficiently with water and dried to give pale yellow solids of 2-(5-methyl-2-thienyl)-5-methyl-N-(1H-tetrazole-5-yl)-4-thiazolecarboxamide (372.9 mg, 97%), m.p. 278°-280° C. (from methanol-THF-water).

Workup

  1. customto react at room temperature for 1 hour
  2. customThe solvent was removed from the reaction mixture
  3. additionthe residue was treated with water
  4. temperaturecooling
  5. filtrationThe produced solids were filtered with suction
  6. washwashed sufficiently with water
  7. customdried

Sources & evidence

ORD record
ord-706a08723415411eb153d00b47942e62
Source dataset
uspto-grants-1989_11
Patent number
US04879295

Reaction notes

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