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

HRID 336196Notes

Reaction equation

HRID 336196 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>C1COCC1.C(OCC)C>[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

Conditions

Temperature
0 °C

Procedure

Thiomorpholine 1,1-dioxide (3 g; 22.192 mmol) is dissolved in THF (70 mL) and cooled to 0° C. Triethylamine (3.708 mL; 26.6 mmol) is added, followed by 20% phosgene in toluene (35.229 mL; 66.6 mmol). The reaction mixture is stirred at room temperature for 18 hours. After this time, the reaction mixture is poured into ethyl ether (200 mL), then filtered through Celite®. The Celite® is washed with ethyl ether several times and the combined filtrates are concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, d-CDCl3): δ 3.1-3.2 (m; 4H), 4.1-4.3 (d, 4H).

Workup

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

Sources & evidence

ORD record
ord-81e05e5b901440919e41e58d6d38edd8
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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