2-Furancarboxylic acid → HCID 178522686, compound

HRID 621816Notes

Reaction equation

HRID 621816 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C.[NH2:28][C:29]1[NH:33][N:32]=[N:31][N:30]=1>C(#N)C>[NH:30]1[C:29]([NH:28][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[O:8])=[N:33][N:32]=[N:31]1

Participants

6

Reactant 4

HCID 69192-Furancarboxylic acidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178509299HCID 178509299, compound

Product 1

HCID 178522686HCID 178522686, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the procedure described in Example 120, 2-furancarboxylic acid (5.00 g, 44.46 mmol) is treated with 1,1'-carbonyl diimidazole (8.31 g, 51.25 mmol, 1.15 equiv), triethylamine (10.9 g, 107.6 mmol, 2.4 equiv) and 5-aminotetrazole (4.51 g, 53.02 mmol, 1.19 equiv) in refluxing (17 hours) acetonitrile (250 mL) to give the crude carbamoyl product. Recrystallization from N,N-dimethyl formamide/water afforded 4.90 g (7.96 g theo., 62%) of N-1H-tetrazol-5-yl-2-furancarboxamide as a white solid; mp 280°-283° C. (dec).

Workup

  1. customto give the crude carbamoyl product
  2. customRecrystallization from N,N-dimethyl formamide/water

Sources & evidence

ORD record
ord-7105baee72c945f8ae99178df6d59614
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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