Sulfuryl chloride → HCID 117664335, compound

HRID 2199489Notes

Reaction equation

HRID 2199489 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].S(Cl)([Cl:25])(=O)=O>C(OCC)C>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([Cl:25])=[C:8](/[CH:14]=[CH:15]/[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 71626584HCID 71626584, compound

Product 1

HCID 117664335HCID 117664335, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve compound 7 (12 g, 0.042 mol) in anhydrous diethyl ether (150 ml), dropwise add in sulfuric chloride (11.2 g, 0.084 mol) at room temperature, when addition finishes, reflux the mixture for 3h, after completion of the reaction, cool the reaction mixture to 0° C., filter out the white solid precipitation to obtain the target product as a white solid (11.4 g, 85%). 1H NMR (400 MHz, CDCl3): 3.82 (s, 3H), 3.94 (s, 3H), 6.48 (d, J=16.0 Hz, 1H), 6.52 (s, 1H), 7.20 (d, J=16.0 Hz, 1H), 7.30 (t, J=8.0 Hz, 1H), 7.38 (t, J=8.0 Hz, 2H), 7.50 (d, J=8.0 Hz, 2H),

Workup

  1. additionwhen addition
  2. customafter completion of the reaction
  3. filtrationfilter out the white solid precipitation

Sources & evidence

ORD record
ord-73dddcf564b94545a4e6e17d794df09b
Source dataset
uspto-grants-2016_06
Patent number
US09359298B2

Reaction notes

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