Dichloromethane → HCID 86624965, compound

HRID 1041877Notes

Reaction equation

HRID 1041877 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N:10]([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[Cl:13].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].[Cl:13][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([CH3:16])([CH3:11])[CH3:12])=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:14]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9526Methyl triflate2×HCID 66909163Methyl 2-chloro-5-(dimethylamino)benzoate

Product 1

HCID 86624965HCID 86624965, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 4.49 g (21.0 mmol) 18a and 75 ml dichloromethane were added 34.5 g (21.0 mmol) methyltriflate (Aldrich) drop wisely. The reaction mixture was stirred for 2 days at room temperature. 17 g (10 mmol) methyltriflate (Aldrich) were added and the reaction mixture was stirred at 40° C. for 20 h. The reaction mixture was cooled to 20° C. and diethylether was added. The desired compound precipitates and the solvent was decanted and 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 18b was obtained in 86% yield (6.78 g, 18.1 mmol).

Workup

  1. stirringthe reaction mixture was stirred at 40° C. for 20 h
  2. temperatureThe reaction mixture was cooled to 20° C.
  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-1328fbaf259d49a1870c09d3b0e5e0d0
Source dataset
uspto-grants-2013_10
Patent number
US08557776B2

Reaction notes

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