Triethylamine → HCID 178434900, compound

HRID 621812Notes

Reaction equation

HRID 621812 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7](O)=[O:8])=[C:4]([O:10][CH:11]([CH3:13])[CH3:12])[C:3]=1[O:14][CH:15]([CH3:17])[CH3:16].C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C.[NH2:37][C:38]1[NH:42][N:41]=[N:40][N:39]=1.C(C1NN=NN=1)(=O)N>C(#N)C>[CH3:1][C:2]1[O:6][C:5]([C:7]([NH:37][C:38]2[NH:42][N:41]=[N:40][N:39]=2)=[O:8])=[C:4]([O:10][CH:11]([CH3:13])[CH3:12])[C:3]=1[O:14][CH:15]([CH3:17])[CH3:16]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 21243561HCID 21243561, compoundHCID 178509299HCID 178509299, compoundHCID 178513865HCID 178513865, compound

Product 1

HCID 178434900HCID 178434900, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the procedure described in Example 120, 2.00 g (8.84 mmol) of the above carboxylic acid, 1.65 g (10.18 mmol, 1.15 equiv) of 1,1'-carbonyl diimidazole, 2.2 g (21.5 mmol, 2.4 equiv) of triethylamine, and 0.89 g (10.46 mmol, 1.18 equiv) of 5-aminotetrazole in refluxing (2.5 hours) acetonitrile (46 mL) is converted to the carbamoyltetrazole. Recrystallization from toluene afforded 0.75 g (2.73 g theo., 27%) of 5-methyl-3,4-diisopropoxy-N-1H-tetrazol-5-yl-2-furancarboxamide; mp 190°-192° C. (dec).

Workup

  1. customRecrystallization from toluene

Sources & evidence

ORD record
ord-81d0d9ec3d254d43b390158fc67b3023
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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