Dichloromethane → HCID 86624959, compound

HRID 1041857Notes

Reaction equation

HRID 1041857 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])=[C:6]([F:13])[CH:5]=1.Cl[CH2:16]Cl.C[O:19][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21]>C(OCC)C>[F:24][C:23]([F:26])([F:25])[S:20]([O-:22])(=[O:21])=[O:19].[F:13][C:6]1[CH:5]=[C:4]([C:3]([O:2][CH3:1])=[O:14])[CH:9]=[CH:8][C:7]=1[N+:10]([CH3:16])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9526Methyl triflateHCID 59847703HCID 59847703, compound

Product 1

HCID 86624959HCID 86624959, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 3.90 g (19.8 mmol) 3a and 70 ml dichloromethane were added 32.5 g (198 mmol) methyltriflate (Aldrich) drop wisely. The reaction mixture was stirred for 2.5 days at room temperature and 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 3b was obtained in 80% yield (5.72 g, 15.84 mmol).

Workup

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

Sources & evidence

ORD record
ord-9a946239cb8f43e7b7587640fba718ac
Source dataset
uspto-grants-2013_10
Patent number
US08557776B2

Reaction notes

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