Ethyl bromoacetate → HCID 19879225, compound

HRID 1885595Notes

Reaction equation

HRID 1885595 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH2:21][CH2:20][CH2:19][N:11]3[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(Cl)Cl>[C:24]([CH2:23][S:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH2:21][CH2:20][CH2:19][N:11]3[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1)([O:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 135962046(4-mercaptophenyl) 3 (4-pyridyl) 6,7dihydro[5H]-pyrrolo[1,2-a]imidazole

Product 1

HCID 19879225HCID 19879225, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 1.0 gm (3.4 mmole) of 2-(4-mercaptophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole in 50 ml methylene chloride at 0° was added a solution of 0.63 g (3.7 mmole, 0.43 ml) ethyl bromoacetate in 10 ml CH2Cl2 over a period of 10 minutes. The reaction was allowed to come to room temperature and was stirred for 30 minutes. The mixture was then diluted with methylene chloride and washed with 3N NaHCO3, saturated NaCl, treated with Na2SO4, stripped, then flash chromatographed on silica with methylene chloride containing 1% to 5% MeOH. The isolated material was recrystallized from ethyl acetate to give 0.35 g of the titled product. 27.2% yield, mp 102°-103° C. Analyzed for C21H21N3O2S, Calculated, C: 66.47, H:5.58, N: 11.07; Found, C: 66.39, H: 5.62, N: 10.97.

Workup

  1. customto come to room temperature
  2. washwashed with 3N NaHCO3, saturated NaCl
  3. additiontreated with Na2SO4
  4. customflash chromatographed on silica with methylene chloride containing 1% to 5% MeOH
  5. customThe isolated material was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f73fdf153c084914a4d9591e3fdcdfc6
Source dataset
uspto-grants-1992_09
Patent number
US05145858

Reaction notes

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