Triethylamine → HCID 53900828, compound

HRID 1591101Notes

Reaction equation

HRID 1591101 reaction equation
[C:1]([C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])=[N:5][C:4]=1C(O)=O)#[N:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CC(O)(C)C>[C:1]([C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])=[N:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 178510660HCID 178510660, compound

Product 1

HCID 53900828HCID 53900828, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 5-cyano-2-(2,4-dichlorophenyl)imidazole-4-carboxylic acid (40.0 g, 0.142 mol), diphenylphosphoryl azide (37.0 g, 0.142 mol) and triethylamine (14.4 g, 19.8 ml, 0.142 mol) in 2-methyl-2-propanol (dried by distillation from calcium hydride, 1400 ml) was heated at reflux for 24 hours. After cooling the mixture was filtered and the filtrate evaporated to dryness. The residue was dissolved in ethyl acetate (2250 ml) and washed with hydrochloric acid (1 M, 250 ml) saturated aqueous sodium bicarbonate solution (2×250 ml) dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was recrystallized from ethanol to give 4-tert.butoxycarbonylamino)-5-cyano-2-(2,4-dichlorophenyl)imidazole (22.2 g) m.p. 185° C. (with decomposition) as an off-white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperatureAfter cooling the mixture
  4. filtrationwas filtered
  5. customthe filtrate evaporated to dryness
  6. dissolutionThe residue was dissolved in ethyl acetate (2250 ml)
  7. washwashed with hydrochloric acid (1 M, 250 ml) saturated aqueous sodium bicarbonate solution (2×250 ml)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. customevaporated to dryness
  10. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-dcccfba8d59e4a7da130e2767b1bacb0
Source dataset
uspto-grants-1993_04
Patent number
US05206257

Reaction notes

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