Dimethylformamide → HCID 86705312, compound

HRID 339853Notes

Reaction equation

HRID 339853 reaction equation
[Na+].[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH2:16][S:17]([O-:20])(=O)=[O:18])[CH:13]=[CH:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN(C)C=O.C(Cl)(=O)C([Cl:29])=O>C1COCC1.C(OCC)C>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH2:16][S:17]([Cl:29])(=[O:20])=[O:18])[CH:13]=[CH:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 131732068HCID 131732068, compound

Product 1

HCID 86705312HCID 86705312, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under inert gas, 2.36 g of (3-benzyloxyphenyl)methanesulfonic acid sodium salt and 0.61 ml of N,N-dimethylformamide were initially charged in 45 ml of THF, then, at a temperature of −20° C., 4.1.73 ml of oxalyl chloride were added dropwise and the reaction solution was allowed to come to 0° C. within 15 minutes. The reaction solution was diluted with 100 ml of diethyl ether and washed with water, dilute aqueous sodium hydrogencarbonate solution and saturated sodium chloride solution. The organic phase was dried over MgSO4 and concentrated by rotary evaporation. The residue (2.30 g) was used in the next reaction without further purification.

Workup

  1. washwashed with water, dilute aqueous sodium hydrogencarbonate solution and saturated sodium chloride solution
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated by rotary evaporation
  4. customThe residue (2.30 g) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-7462229d6ce945e594445b5ebaa26443
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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