Dimethylformamide → HCID 86705294, compound

HRID 339825Notes

Reaction equation

HRID 339825 reaction equation
[Na+].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][S:17]([O-:20])(=O)=[O:18])=[CH:12][CH:11]=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:15]=[CH:14][C:13]([CH2:16][S:17]([Cl:29])(=[O:20])=[O:18])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 131732067HCID 131732067, compound

Product 1

HCID 86705294HCID 86705294, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under inert gas, 5.70 g of (4-benzyloxyphenyl)methanesulfonic acid sodium salt and 1.48 ml of N,N-dimethylformamide were initially charged in 110 ml of THF, then, at a temperature of −20° C., 4.17 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 (4.89 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 (4.89 g) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-1d14c8e9362b49e39ab808b1a10b4dfb
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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