Thionyl Chloride → 4-[3-(4-Tert-butylaminocarbonylphenyl)-3-chloroprop-1-yl]-1-tritylimidazole

HRID 22563Notes

Reaction equation

HRID 22563 reaction equation
[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[CH2:15][CH2:16][C:17]2[N:18]=[CH:19][N:20]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:21]=2)=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:44])=O>C(Cl)Cl>[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]([Cl:44])[CH2:15][CH2:16][C:17]2[N:18]=[CH:19][N:20]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:21]=2)=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 140972094-[3-(4-Tert-butylaminocarbonylphenyl)-3-hydroxyprop-1-yl]-1-tritylimidazole

Product 1

HCID 140972104-[3-(4-Tert-butylaminocarbonylphenyl)-3-chloroprop-1-yl]-1-tritylimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.21 g of 4-[3-(4-tert-butylaminocarbonylphenyl)-3-hydroxyprop-1-yl]-1-tritylimidazole and 1.5 ml of thionyl chloride in 50 ml of methylene chloride is refluxed for 1 h, cooled and poured into 50 ml of ice-cold sodium bicarbonate solution. The organic phase is separated, dried over sodium sulfate and evaporated to yield 4-[3-(4-tert-butylaminocarbonylphenyl)-3-chloroprop-1-yl]-1-tritylimidazole as a white foam. NMR (CDCl3): δ=1.45 (s, 9H), 4.30 (t, J=6.0 Hz, 2H).

Workup

  1. temperaturecooled
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-fd102046d15a48eca63404f9073823aa
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Reaction notes

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