Triethylamine → HCID 15405454, compound

HRID 327002Notes

Reaction equation

HRID 327002 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9](Cl)(=[O:11])=[O:10].[OH:13][CH2:14][P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18].C(N(CC)CC)C.S(Cl)(Cl)(=O)=O>CCOCC.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([O:13][CH2:14][P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])(=[O:10])=[O:11]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 76513Diethyl phosphonomethanolHCID 157253702-Chloro-6-methylbenzene-1-sulfonyl chloride

Product 1

HCID 15405454HCID 15405454, compoundYield 87.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4.63 g of 2-chloro-6-methylbenzenesulfonyl chloride dissolved in 20 ml of anhydrous ether was added dropwise over a 15 minute period to a mixture of 3.50 g of diethyl P-(hydroxymethyl)phosphonate (Example 17), 5 ml of triethylamine and 15 ml of anhydrous ether. The addition was mildly exothermic and a white precipitate began to form shortly after the addition of the sulfonyl chloride was begun. The reaction was stirred at room temperature overnight. After 48 hours of additional stirring the reaction solution was diluted with 200 ml of ethyl acetate and 80 ml of water. The organic phase was washed with two 90 ml portions of water, dried with magnesium sulfate, filtered and concentrated to yield 6.4 g of an oil which solidified upon standing, mp 41°-43° C.

Workup

  1. additionThe addition
  2. customto form shortly
  3. stirringAfter 48 hours of additional stirring the reaction solution
  4. washThe organic phase was washed with two 90 ml portions of water
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0d01e251672f4789a72338a3ae6116cf
Source dataset
uspto-grants-1993_12
Patent number
US05272128

Reaction notes

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