Carbon Tetrachloride → HCID 86761064, compound

HRID 2243382Notes

Reaction equation

HRID 2243382 reaction equation
[SH:1][CH:2](C)[C:3]([OH:5])=[O:4].[SH:7][CH:8](C)[C:9]([OH:11])=[O:10].SC(C)[C:15]([OH:17])=[O:16].[CH2:19]([C:21]([CH2:26][OH:27])([CH2:24][OH:25])[CH2:22][CH3:23])[OH:20].ClN1C(=O)CCC1=O.[C:36]([Cl:40])(Cl)(Cl)Cl>>[S:7]=[CH:8][CH:36]([Cl:40])[C:3]([OH:5])=[O:4].[S:1]=[CH:2][CH:36]([Cl:40])[C:9]([OH:11])=[O:10].[S:1]=[CH:2][CH:36]([Cl:40])[C:15]([OH:17])=[O:16].[CH2:19]([C:21]([CH2:26][OH:27])([CH2:24][OH:25])[CH2:22][CH3:23])[OH:20]

Participants

4

Reactant 3

HCID 5943Carbon Tetrachloride2×HCID 31398ChlorosuccinimideHCID 86761065HCID 86761065, compound

Product 1

HCID 86761064HCID 86761064, compound

Procedure

A solution of trimethylolpropane tris(mercaptopropionate) (4.0 grams, 0.010 mol.) in carbon tetrachloride (10 milliliters) was added dropwise to a slurry of N-chlorosuccinimide (4.15 grams, 0.031 mol.) and carbon tetrachloride (30 milliliters) in a 3-neck round bottom flask equipped with a magnetic stir-bar, nitrogen inlet, pressure-equalizing dropping funnel and a thermocouple. The exothermic reaction was controlled to less than 27° C. using an ice-bath. The mixture was allowed to stir at ambient temperature for an additional 5 hours. The reaction mixture was filtered to remove succinimide by-product to give a yellow solution of trimethylolpropane tris(3-sulfenylchloropropionate). 1H NMR (CDCl3) δ: 4.09 (s, 6H), 3.37 (m, 6H), 2.89 (t, J=6.5 Hz, 6H); 1.52 (q, J=6.5 Hz, 2H); 0.96 (t, J=7.4 Hz, 3H). 13C NMR (CDCl3): 170.8, 64.2, 41.4, 36.7, 33.7, 23.3, 7.8 ppm.

Workup

  1. customequipped with a magnetic stir-bar, nitrogen inlet
  2. customThe exothermic reaction
  3. customwas controlled to less than 27° C.
  4. filtrationThe reaction mixture was filtered
  5. customto remove succinimide by-product

Sources & evidence

ORD record
ord-5e4a6698d287428d8361560124f049aa
Source dataset
uspto-grants-2010_03
Patent number
US07674861B1

Reaction notes

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