Sulfolane → HCID 21916253, compound

HRID 2180374Notes

Reaction equation

HRID 2180374 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17](=[O:28])[NH:18][C:19]2[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=2[CH3:27])[C:8](Br)=[N:9][C:10]=1[C:11](F)(F)F)=O)C.S1([CH2:35][CH2:34][CH2:33][CH2:32]1)(=O)=O>[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[CH:34]1([CH2:35][N:7]([CH2:6][CH2:10][CH3:11])[C:4]([C:6]2[N:7]3[CH2:16][C:17](=[O:28])[N:18]([C:19]4[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=4[CH3:27])[C:8]3=[N:9][C:10]=2[CH3:11])=[O:3])[CH2:32][CH2:33]1

Participants

4

Reactant 2

HCID 31347SulfolaneHCID 20780216HCID 20780216, compound

Product 1

HCID 21916253HCID 21916253, compound

Reagents, catalysts & solvents 1

HCID 76223Silver(I) trifluoromethanesulfonateCatalyst

Conditions

Temperature
150 °C

Procedure

A suspension of 2-bromo-5-trifluoromethyl-3-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-3H-imidazole-4-carboxylic acid ethyl ester (20.12 g, 0.044 mmol) and silver triflate (11.87 g, 0.046 mol) in sulfolane (200 mL) was heated at 150° C. for 6 h. The resulting reaction mixture was cooled to room temperature and filtered through a short pad of celite. The final purification was achieved by a reverse-phase preparative HPLC to give the desired product as yellowish solid. Yield−5.24 g (24%). LC/MS: tR=1.89 min., MS: [M+H]=382. 6-Chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazole-3-carboxylic acid ethyl ester, scheme 6: (AA)

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas cooled to room temperature
  3. filtrationfiltered through a short pad of celite
  4. customThe final purification

Sources & evidence

ORD record
ord-e50b5c80fbfd4088878502a9bf76f6a5
Source dataset
uspto-grants-2005_05
Patent number
US06888004B2

Reaction notes

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