Pivaloyl chloride → 2-(4-Trimethylacetylthiophenyl)3-(4-pyridyl)-6,7-dihydro [5H]-pyrrolo[1,2 a]imidazole

HRID 1885591Notes

Reaction equation

HRID 1885591 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.[CH3:22][C:23]([CH3:28])([CH3:27])[C:24](Cl)=[O:25]>C(Cl)Cl>[CH3:22][C:23]([CH3:28])([CH3:27])[C:24]([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:25]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 135962046(4-mercaptophenyl) 3 (4-pyridyl) 6,7dihydro[5H]-pyrrolo[1,2-a]imidazole

Product 1

HCID 198792172-(4-Trimethylacetylthiophenyl)3-(4-pyridyl)-6,7-dihydro [5H]-pyrrolo[1,2 a]imidazoleYield 33.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 1.0 g (3.4 mmole) of 2-(4-mercaptophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a] imidazole prepared as in Example 16 in 50 ml methylene chloride at 0° C. was added a solution of 0.3 g (3.7 mmole, 0.26 ml) trimethylacetyl chloride 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 0.43 g of the titled compound. 33.5% yield, mp 216°-217.5° C. C22H23N3OS, Calculated, C: 70.00, H: 6.14, N: 11.13; Found, C: 70.01, H: 6.20, N: 10.99.

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-cdb95a15dc0c41379f8359cdd484a34a
Source dataset
uspto-grants-1992_09
Patent number
US05145858

Reaction notes

Loading…