Triethylamine → HCID 86645755, compound

HRID 885465Notes

Reaction equation

HRID 885465 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:13]2[C:8](=[CH:9][C:10]([C:14]#[N:15])=[CH:11][CH:12]=2)[CH2:7][O:6]1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[CH3:31][S:32]([O:1][CH2:2][CH2:3][CH2:4][C:5]1([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[C:13]2[C:8](=[CH:9][C:10]([C:14]#[N:15])=[CH:11][CH:12]=2)[CH2:7][O:6]1)(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67543090HCID 67543090, compound

Product 1

HCID 86645755HCID 86645755, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15.0 g (48.5 mmol) of the 1-(3-hydroxypropyl)-1-(4-methoxyphenyl)-1,3-dihydro-5-isobenzofurancarbonitrile prepared in step 5 was dissolved in 200 ml of dichloromethane, and 7.4 g (727 mmol) of triethylamine and 6.7 g (58.2 mol) of methanesulfonylchloride were added dropwise at 0° C. The solution was then stirred for 1 hr. The reaction mixture was washed with water and saturated NaCl solution. An organic layer was dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure to afford 18.2 g of the yellow target compound (yield: 79%). The compound thus obtained was used in the next reaction without further purification.

Workup

  1. washThe reaction mixture was washed with water and saturated NaCl solution
  2. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9ed852c9f89b43a086659aae1eb61cdb
Source dataset
uspto-grants-2012_08
Patent number
US08242159B2

Reaction notes

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