Triethylamine → HCID 178429023, compound

HRID 621815Notes

Reaction equation

HRID 621815 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:13][C:14]1[NH:18][N:17]=[N:16][N:15]=1.C(N(CC)CC)C.[CH3:26][C:27]1[O:31][C:30]([C:32](O)=[O:33])=[C:29]([O:35][CH:36]([CH3:38])[CH3:37])[CH:28]=1.C(C1NN=NN=1)(=O)N>C(#N)C>[CH3:26][C:27]1[O:31][C:30]([C:32]([NH:13][C:14]2[NH:18][N:17]=[N:16][N:15]=2)=[O:33])=[C:29]([O:35][CH:36]([CH3:38])[CH3:37])[CH:28]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 21243563HCID 21243563, compoundHCID 178509299HCID 178509299, compoundHCID 178513865HCID 178513865, compound

Product 1

HCID 178429023HCID 178429023, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the procedure described in Example 120, 0.60 g (3.7 mmol, 1.1 equiv) of 1,1'-carbonyl diimidazole, 0.33 g (3.9 mmol, 1.2 equiv) of 5-aminotetrazole and 0.80 g (7.9 mmol, 2.4 equiv) of triethylamine in refluxing (16 hours) acetonitrile (15 mL) are used to convert 0.61 g (3.3 mmol) of the carboxylic acid described above to 0.45 g of the carbamoyltetrazole as a tan solid. Recrystallization gave 0.35 g (1.26 g theo., 28% overall) of analytically pure 5-methyl-3-isopropoxy-N-1H-tetrazol-5-yl-2-furancarboxamide as a tan, crystalline solid; mp 240°-242° C. (dec).

Workup

  1. customRecrystallization

Sources & evidence

ORD record
ord-0fa87bbd1ed8458fbac917f36759659b
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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