Triethylamine → HCID 13457982, compound

HRID 462675Notes

Reaction equation

HRID 462675 reaction equation
C[C:2]([CH3:16])([CH2:6][C:7]1[NH:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=1)[C:3](O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.C([N:36]([CH2:39]C)CC)C>C(O)(C)(C)C>[CH3:16][C:2]1([CH3:3])[CH2:6][C:7]2=[N:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]2[C:39](=[O:24])[NH:36]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 499410995242-09-4

Product 1

HCID 13457982HCID 13457982, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution containing 11.2 g of this benzimidazolepropanoic acid (0.05 mole), diphenylphosphorylazide (14.0 g, 0.05 mole) and triethylamine (5.0 g, 0.0 mole) in 100 mL of t-butanol was heated at reflux for 10 hr. The volatile material was evaporated at 100° and 30 torr and the residue was diluted with ethanol-methylene chloride. Filtration of the chilled mixture provided a total of 6.5 g of 3,4-dihydro-3,3-dimethylpyrimido{1,6-a}benzimidazol-1(2H)-one as a white solid, m.p. 205°-210°. This material can be purified by reprecipitation from acid solution using 20% NaOH to afford white flakes, m.p. 211°-215°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 hr
  3. customThe volatile material was evaporated at 100°
  4. addition30 torr and the residue was diluted with ethanol-methylene chloride
  5. filtrationFiltration of the chilled mixture

Sources & evidence

ORD record
ord-ab9b2e1ea7cf4b668cd55a6803a2b973
Source dataset
uspto-grants-1985_05
Patent number
US04517188

Reaction notes

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