Dichloromethane → HCID 58310938, compound

HRID 1189577Notes

Reaction equation

HRID 1189577 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1[N:7]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:8]([CH3:27])=[CH:9][C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19].ClCCl.C([O-])(O)=O.[Na+]>C(#N)C>[C:1]([C:9]1[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)(=[O:20])=[O:19])=[C:6]([CH3:5])[N:7]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:8]=1[CH3:27])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 58310962HCID 58310962, compound

Product 1

HCID 58310938HCID 58310938, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a round-bottomed flask equipped with a magnetic stir bar, acetyl chloride (1.7 μL, 0.024 mmol) was added to a solution of ethyl 2-(2,5-dimethyl-3-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (10 mg, 0.024 mmol) in acetonitrile (0.5 mL) at room temperature. The reaction was stirred for 5 minutes, then dichloromethane (10 mL) and NaHCO3 (sat. aq. 10 mL) were added. The dichloromethane layer was separated and dried over Na2SO4, filtered and concentrated to yield ethyl 2-(3-acetyl-2,5-dimethyl-4-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (8 mgs, 72%).

Workup

  1. customIn a round-bottomed flask equipped with a magnetic stir bar
  2. customThe dichloromethane layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-18237d88e9354a979016988b1f811ddb
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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