Dimethyl Sulfoxide → HCID 178522728, compound

HRID 1638323Notes

Reaction equation

HRID 1638323 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.CS(C)=O.[NH2:30][C:31]1[NH:35][N:34]=[N:33][N:32]=1>CN(C=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[C:9]([C:11]([NH:30][C:31]2[NH:35][N:34]=[N:33][N:32]=2)=[O:13])[N:10]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 682631,1'-CarbonyldiimidazoleHCID 156230722-(2-Furyl)thiazolidine-4-carboxylic acid, 97%HCID 178509299HCID 178509299, compound

Product 1

HCID 178522728HCID 178522728, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-(2-furyl)-4-thiazolecarboxylic acid (300 mg) and CDI (373.8 mg) in a mixed solvent of dry DMF (10 mg) and dry DMSO (2 ml) was prepared at 100° C. and allowed to react under the same condition for 1 hour. Then a solution of 5-aminotetrazole (156.9 mg) in dry DMF (2 ml) was added dropwise thereto and the reaction was continued for additional 3 hours. The solvent was removed from the reaction mixture. The residue was treated with water and acidified with 2N-HCl. The produced solids were filtered, washed sufficiently with water and then with ether, and dried to give yellow ocher solids of 2-(2-furyl)-N-(1H-tetrazole-5-yl)-4-thiazolecarboxamide (174 mg, 43%), m.p. 275°-277° C.

Workup

  1. customto react under the same condition for 1 hour
  2. customThe solvent was removed from the reaction mixture
  3. additionThe residue was treated with water
  4. filtrationThe produced solids were filtered
  5. washwashed sufficiently with water
  6. dry with materialwith ether, and dried

Sources & evidence

ORD record
ord-bf8da9621a6e4b7d83a0871254307cc4
Source dataset
uspto-grants-1989_11
Patent number
US04879295

Reaction notes

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