tert-Butanol → HCID 18947715, compound

HRID 1769301Notes

Reaction equation

HRID 1769301 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:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C.[CH3:43][C:44]([OH:47])([CH3:46])[CH3:45]>>[C:44]([O:47][C:41]([NH:38][C:4]1[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[NH:7][C:3]=1[C:1]#[N:2])=[O:26])([CH3:46])([CH3:45])[CH3:43]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 178510660HCID 178510660, compound

Product 1

HCID 18947715HCID 18947715, compound

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 (1M, 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-(2,4dichlorophenyl)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 (1M, 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-41bb49d208f04e3fb4d189ac1c2939f9
Source dataset
uspto-grants-1995_01
Patent number
US05380865

Reaction notes

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