Dimethylformamide → HCID 58201252, compound

HRID 511982Notes

Reaction equation

HRID 511982 reaction equation
[Na+:1].[O:2]([CH2:9][CH2:10][CH2:11][CH2:12][S:13]([O-:16])(=[O:15])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S(Cl)([Cl:19])=O.CN(C=O)C>C1C=CC=CC=1>[O:2]([CH2:9][CH2:10][CH2:11][CH2:12][S:13]([Cl:19])(=[O:16])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Na+:1].[O:2]([CH2:9][CH2:10][CH2:11][CH2:12][S:13]([O-:16])(=[O:14])=[O:15])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 58201252HCID 58201252, compound

Product 2

HCID 25017609HCID 25017609, compoundHCID 58201252HCID 58201252, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Phenoxybutyl sulfonyl chloride (16) was synthesized as described in 12.1 using 15 (1.0 g, 4.37 mmol) and thionyl chloride (1.55 g, 13.0 mmol) in benzene (40 mL)/DMF (4 mL). Purification by flash column chromatography on silica gel afforded 15 (0.434 g, 40% yield) as a white solid (m p 65-67° C.).

Workup

  1. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-054e08bb27f440e68aba63164bd81b64
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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