4-bromo-N-tert-butylbenzamide → 4-[3-(4-Tert-butylaminocarbonylphenyl)-3-hydroxyprop-1-yl]-1-tritylimidazole

HRID 568556Notes

Reaction equation

HRID 568556 reaction equation
C([Li])CCC.[C:6]([NH:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1)([CH3:9])([CH3:8])[CH3:7].[C:20]([N:39]1[CH:43]=[C:42]([CH2:44][CH2:45][CH:46]=[O:47])[N:41]=[CH:40]1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCCCCC.O1CCCC1>[C:6]([NH:10][C:11]([C:12]1[CH:17]=[CH:16][C:15]([CH:46]([OH:47])[CH2:45][CH2:44][C:42]2[N:41]=[CH:40][N:39]([C:20]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:43]=2)=[CH:14][CH:13]=1)=[O:19])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 6032584-bromo-N-tert-butylbenzamideHCID 114514283-(1-Tritylimidazol-4-YL) propionaldehydeHCID 178418339Butyllithium

Product 1

HCID 140972094-[3-(4-Tert-butylaminocarbonylphenyl)-3-hydroxyprop-1-yl]-1-tritylimidazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 25 mmoles of n-butyllithium in 10 ml of hexane is added dropwise to a solution of 3.19 g of N-tert-butyl 4-bromobenzamide in 250 ml of tetrahydrofuran at -70° under argon. After 30 min, a solution of 3.74 g of 3-(1-tritylimidazol-4-yl)propionaldehyde in 100 ml of tetrahydrofuran is added slowly. The reaction mixture is stirred at -70° for 30 min, allowed to warm to 25°, stirred at 25° for 2.5 h and quenched with excess saturated ammonium chloride solution. The aqueous layer is separated and extracted with methylene chloride (2×100 ml). The combined organic extracts are dried over sodium sulfate and evaporated. The residue is chromatographed on 220 g of silica with 5:1 ether:ethyl acetate to yield 4-[3-(4-tert-butylaminocarbonylphenyl)-3-hydroxyprop-1-yl]-1-tritylimidazole as an oil. IR (CH2Cl2): 1660 cm-1.

Workup

  1. temperatureto warm to 25°
  2. stirringstirred at 25° for 2.5 h
  3. customquenched with excess saturated ammonium chloride solution
  4. customThe aqueous layer is separated
  5. extractionextracted with methylene chloride (2×100 ml)
  6. dry with materialThe combined organic extracts are dried over sodium sulfate
  7. customevaporated
  8. customThe residue is chromatographed on 220 g of silica with 5:1 ether

Sources & evidence

ORD record
ord-950f77ea4a084ff7b276f4e360dca669
Source dataset
uspto-grants-1988_03
Patent number
US04728645

Reaction notes

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