Toluene → 1,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl chloride

HRID 469715Notes

Reaction equation

HRID 469715 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:16](Cl)([Cl:18])=[O:17].C1(C)C=CC=CC=1>O1CCCC1.CCOCC>[O:7]=[S:4]1(=[O:8])[CH2:5][CH2:6][N:1]([C:16]([Cl:18])=[O:17])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 6484228Thiomorpholine 1,1-dioxide

Product 1

HCID 216949071,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Thiomorpholine 1,1-dioxide (1 g; 7.397 mmol) is dispersed in tetrahydrofuran (50 mL) followed by the addition of triethylamine (1.238 mL; 8.88 mmol) and 20% phosgene in toluene (11.743 mL; 22.2 mmol). The reaction mixture is stirred at room temperature overnight. After this time, the mixture is diluted with ether and filtered through Celite®. The Celite® is washed with ether several times and the combined filtrates are concentrated in vacuo to afford title compound as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 3.15 (4H, m), 4.13 (2H, s), 4.24 (2H, s).

Workup

  1. filtrationfiltered through Celite®
  2. washThe Celite® is washed with ether several times
  3. concentrationthe combined filtrates are concentrated in vacuo

Sources & evidence

ORD record
ord-279b23f6195847d981dca79469f393cc
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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