Diethyl Ether → HCID 87499731, compound

HRID 1516969Notes

Reaction equation

HRID 1516969 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[S:11]([Cl:14])(=[O:13])=[O:12].[OH:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.S(Cl)(Cl)(=O)=O.CCOCC>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[O:7])=[CH:4][C:3]=1[S:11]([Cl:14])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24648Sulfuryl chlorideHCID 611632-MorpholinoethanolHCID 156326894-Chloro-3-(chlorosulfonyl)benzoyl chloride

Product 1

HCID 87499731HCID 87499731, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-chloro-3-(chlorosulfonyl)benzoyl chloride (1.0 g, 3.6 mmol) in DCM (10 ml) was added a solution of hydroxy ethyl morpholine (443 μl, 3.6 mmol) in DCM (1 ml). The reaction mixture was stirred for 12 h after which time no sulfonyl chloride was observed by LC-MS. Upon concentration of the crude reaction mixture a solid was isolated, which was trituated with ether to afford the desired compound as a brown solid. (1.54 g, 100%) IR (neat) vmax/cm−1 1724, 1174, 1450; 6H (500 MHz, DMSO-d6) 8.49 (1H, d, 1.8 Hz), 7.97 (1H, dd, 8.2, 1.9 Hz), 7.56 (1H, d, 8.2 Hz), 4.38-5.00 (2H, m), 3.88-4.07 (2H, m), 3.76-3.83 (2H, m), 3.56-3.62 (2H, m), 3.36-3.54 (2H, m), 3.14-3.28 (2H, m).

Workup

  1. customUpon concentration of the crude reaction mixture a solid
  2. customwas isolated

Sources & evidence

ORD record
ord-2dc9258014354394babef2e98d66c0e6
Source dataset
uspto-grants-2012_07
Patent number
US08227639B2

Reaction notes

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