Triethylamine → HCID 13822973, compound

HRID 977898Notes

Reaction equation

HRID 977898 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[CH3:25][S:26]([O:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 138229722-(2-hydroxyethyl)-N-(1,1-dimethylethyl)benzenesulfonamide

Product 1

HCID 13822973HCID 13822973, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

The alcohol from Example 1 (33.1 g) and 20 ml of triethylamine were dissolved in 350 ml of dichloromethane, cooled to 0° C., and treated with 11 ml methanesulfonyl chloride. After being stirred at room temperature for about 20 hours, the reaction mixture was diluted with dichloromethane (100 ml) and the organic layer was washed with three 50-ml portions of water and one of brine. Drying and concentration in vacuo gave the crude product which gradually crystallized upon standing. The solid was washed with diethyl ether, filtered, and dried to yield 12.0 g of 2-[2-(methylsulfonyloxy)ethyl]-N-(1,1-dimethylethyl)benzenesulfonamide as a white powder; m.p. 106°-108° C.

Workup

  1. washthe organic layer was washed with three 50-ml portions of water and one of brine
  2. customDrying
  3. concentrationconcentration in vacuo
  4. customgave the crude product which
  5. customgradually crystallized
  6. washThe solid was washed with diethyl ether
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-596babbebc2d431194fb27bb7f10e09f
Source dataset
uspto-grants-1987_05
Patent number
US04662933

Reaction notes

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