Dichloromethane → HCID 86624961, compound

HRID 1041860Notes

Reaction equation

HRID 1041860 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH3:12])[CH3:11])=[CH:6][C:5]=1[F:13].Cl[CH2:16]Cl.C[O:19][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21].ClC(Cl)C>C(OCC)C>[F:24][C:23]([F:26])([F:25])[S:20]([O-:22])(=[O:21])=[O:19].[F:13][C:5]1[CH:6]=[C:7]([N+:10]([CH3:16])([CH3:11])[CH3:12])[CH:8]=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:14]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 63651,1-DichloroethaneHCID 9526Methyl triflateHCID 66909119HCID 66909119, compound

Product 1

HCID 86624961HCID 86624961, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2.46 g (12.5 mmol) 4a and 50 ml dichloromethane were added 20.5 g (125 mmol) methyltriflate (Aldrich) drop wisely. The reaction mixture was refluxed for 2 days. The solvent was carefully substituted by dichloroethan. The reaction mixture was refluxed for 2 days and then cooled to room temperature. Diethylether was added. The desired compound precipitates and the solvent was decanted. The solid was washed extensively (ten times) with large amounts of diethylether. The solid was dried by use of oil pump vacuum and purified by (C-18) RP-column chromatography (acetonitril/water-gradient 1:99 to 80:20). The desired compound 4b was obtained in 80% yield (3.61 g, 10.0 mmol).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 days
  2. temperatureThe reaction mixture was refluxed for 2 days
  3. customThe desired compound precipitates
  4. customthe solvent was decanted
  5. washThe solid was washed extensively (ten times) with large amounts of diethylether
  6. customThe solid was dried by use of oil pump vacuum
  7. custompurified by (C-18) RP-column chromatography (acetonitril/water-gradient 1:99 to 80:20)

Sources & evidence

ORD record
ord-99ce2ffac06a48348e86f238516055bd
Source dataset
uspto-grants-2013_10
Patent number
US08557776B2

Reaction notes

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