Sulfuryl chloride → HCID 86666540, compound

HRID 1397127Notes

Reaction equation

HRID 1397127 reaction equation
[C:1](=[O:20])([O:5][CH2:6][O:7][C:8](=[O:19])[CH2:9][CH2:10][P:11]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12])SCC.S(Cl)([Cl:24])(=O)=O>>[CH2:14]([O:13][P:11]([CH2:10][CH2:9][C:8]([O:7][CH2:6][O:5][C:1]([Cl:24])=[O:20])=[O:19])([O:16][CH2:17][CH3:18])=[O:12])[CH3:15]

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 86666539S-Ethyl 3-(diethylphosphono)propionyloxymethyl carbonothioate

Product 1

HCID 86666540HCID 86666540, compound

Conditions

Temperature
0 °C

Procedure

To a solution of carbonothioate 80 (1.29 g, 3.93 mmol) in ice-cold CH2Cl2 (20 mL) was added sulfuryl chloride (478 μL, 5.89 mmol) and the mixture was stirred at 0° C. for 2 h 35 min, after which the mixture was concentrated to dryness, providing chloroformate 81 as a colorless gum (1.44 g, >quant.) which was used directly in the next step: 1H NMR (400 MHz, CDCl3) δ 1.33 (t, J=7.1 Hz, 6H), 2.05-2.14 (m, 2H), 2.68-2.75 (m, 2H), 4.07-4.15 (m, 4H), 5.84 (s, 2H): 31P NMR (162 MHz, CDCl3) δ 30.08 (s).

Workup

  1. concentrationafter which the mixture was concentrated to dryness

Sources & evidence

ORD record
ord-e99e4115589b47e9b69596fc645a20e4
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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