Sulfuryl chloride → HCID 86641298, compound

HRID 1841914Notes

Reaction equation

HRID 1841914 reaction equation
S(Cl)([Cl:4])(=O)=O.[C:6](=[O:34])([O:10][CH2:11][O:12][C:13](=[O:33])[CH2:14][CH2:15][CH:16]([P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[P:17]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:18])SCC>>[CH2:20]([O:19][P:17]([CH:16]([P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[CH2:15][CH2:14][C:13]([O:12][CH2:11][O:10][C:6]([Cl:4])=[O:34])=[O:33])([O:22][CH2:23][CH3:24])=[O:18])[CH3:21]

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 86641299HCID 86641299, compound

Product 1

HCID 86641298HCID 86641298, compound

Procedure

Sulfuryl chloride (687 μL, 8.49 mmol) was added drop-wise to 61 (2.03 g, 4.24 mmol). The neat reaction was stirred at room temperature for 2.5 hr. The excess sulfuryl chloride was removed under reduced pressure resulting in chloroformate 62 (1.87 g, 97%) that was used without purification. 1H NMR (400 MHz, CDCl3): δ 1.35 (t, J=7.1, 12H), 2.17-2.36 (m, 2H), 2.53 (tt, J=23.8, 6.5, 1H), 2.80 (t, J=7.5, 2H), 4.15-4.24 (m, 8H), 5.82 (s, 2H). 31P NMR (162 MHz, CDCl3) δ 23.72 (s, 2P).

Workup

  1. customThe neat reaction
  2. customThe excess sulfuryl chloride was removed under reduced pressure
  3. customresulting in chloroformate 62 (1.87 g, 97%) that
  4. customwas used without purification

Sources & evidence

ORD record
ord-4c4acbe995614199b0b3e771cfdfc26c
Source dataset
uspto-grants-2015_02
Patent number
US08946144B2

Reaction notes

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