Triethylamine → HCID 18981707, compound

HRID 1440740Notes

Reaction equation

HRID 1440740 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].[CH2:13]([P:16](=[O:22])([CH2:19][CH2:20][CH3:21])[CH2:17][OH:18])[CH2:14][CH3:15].C(N(CC)CC)C>C1COCC1.C(Cl)Cl.C(OCC)(=O)C>[CH2:13]([P:16](=[O:22])([CH2:19][CH2:20][CH3:21])[CH2:17][O:18][S:9]([C:3]1[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:10])=[O:11])[CH2:14][CH3:15]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 157253702-Chloro-6-methylbenzene-1-sulfonyl chlorideHCID 18981637HCID 18981637, compound

Product 1

HCID 18981707HCID 18981707, compoundYield 21.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7.20 g of 2-chloro-6-methylbenzenesulfonyl chloride dissolved in 30 ml of THF was added dropwise over 30 minutes to a reaction mixture 5.80 g of di-n-propyl(hydroxymethyl)-phosphine oxide, (Example 23), 30 ml of THF, and 4.04 g of triethylamine. The addition caused a mild exotherm and the reaction was allowed to stir at room temperature over the weekend. Most of the THF was removed and the resulting material was partitioned between 200 ml of ethyl acetate and 70 ml of water, the organic phase rewashed with an additional 70 ml of water, dried with magnesium sulfate, filtered and concentrated to yield 6.5 g of the crude desired product as a dark tan oil. The crude product was diluted with 4 ml of methylene chloride and flash chromatographed on Merck silica gel (230-400 mesh) using blends of isopropanol and ethyl acetate, similar fractions were combined and concentrated under reduced pressure to yield the partially purified product. This material was dissolved in 150 ml of ethyl acetate, washed with three 50 ml portions of water, dried with magnesium sulfate, filtered and concentrated to yield 2.4 g of the desired product as a white solid: melting point 51°-53° C.

Workup

  1. additionThe addition
  2. customMost of the THF was removed
  3. customthe resulting material was partitioned between 200 ml of ethyl acetate and 70 ml of water
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield 6.5 g of the crude desired product as a dark tan oil
  8. customchromatographed on Merck silica gel (230-400 mesh)
  9. concentrationconcentrated under reduced pressure
  10. customto yield the partially purified product
  11. washwashed with three 50 ml portions of water
  12. dry with materialdried with magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-8c38e2f7f17448ce81265be51034de4f
Source dataset
uspto-grants-1996_03
Patent number
US05500405

Reaction notes

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