Triethylamine → HCID 178439055, compound

HRID 1460997Notes

Reaction equation

HRID 1460997 reaction equation
O.[NH2:2][C:3]1[NH:7][N:6]=[N:5][N:4]=1.C(N(CC)CC)C.[CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([CH3:26])[CH3:25])[C:19]=1[N:27]=[C:28]=[O:29])([CH3:17])[CH3:16]>C1(C)C=CC=CC=1>[CH3:17][CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([CH3:25])[CH3:26])[C:19]=1[NH:27][C:28]([NH:2][C:3]1[NH:7][N:6]=[N:5][N:4]=1)=[O:29])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 922592,6-Diisopropylphenyl isocyanateHCID 178509300HCID 178509300, compound

Product 1

HCID 178439055HCID 178439055, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Aminotetrazole hydrate (45 g, 0.44 mol) was refluxed in toluene (300 mL) in the presence of a Dean-Stark trap. After removal of the theoretical amount of water (7.9 mL) the mixture was allowed to cool, concentrated in vacuo, and the resulting solid stirred with acetonitrile (500 mL). Triethylamine (61 mL, 0.44 mol) and 2,6-diisopropyl phenylisocyanate (89.3 mL, 0.44 mol) were added sequentially and the mixture refluxed for 4 hours. The mixture was then allowed to cool, concentrated in vacuo to about 200 mL, and acidified with 1M citric acid. The solid was filtered, washed with water (1L), ethyl acetate (1L), and dried in vacuo to give the title compound (b), m.p. >240° C.

Workup

  1. customAfter removal of the theoretical amount of water (7.9 mL) the mixture
  2. temperatureto cool
  3. concentrationconcentrated in vacuo
  4. temperaturethe mixture refluxed for 4 hours
  5. temperatureto cool
  6. concentrationconcentrated in vacuo to about 200 mL
  7. filtrationThe solid was filtered
  8. washwashed with water (1L), ethyl acetate (1L)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-2c66065286244c20a5b58a4c1c2f0663
Source dataset
uspto-grants-1991_12
Patent number
US05073565

Reaction notes

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