Methyl iodide → HCID 13923710, compound

HRID 622300Notes

Reaction equation

HRID 622300 reaction equation
[CH3:1]C(C)([O-])C.[K+].[OH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])=[O:17].CI>O1CCCC1.CCOCC>[CH3:1][O:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])=[O:17]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 138229722-(2-hydroxyethyl)-N-(1,1-dimethylethyl)benzenesulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 13923710HCID 13923710, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 37.0 g of potassium t-butoxide in 400 ml dry tetrahydrofuran was cooled to 0° and a solution of 39.2 g of the product from Example 1 in 300 ml tetrahydrofuran was added dropwise. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After cooling to 0°, 9.3 ml of methyl iodide was added dropwise and the mixture stirred for 15 minutes at 0°. The solution was diluted with ether, washed with water and dried (Na2SO4). Concentration gave a viscous brown oil which was used in the following example, without further purification.

Workup

  1. temperaturewas cooled to 0°
  2. additionAfter the addition
  3. temperatureAfter cooling to 0°
  4. stirringthe mixture stirred for 15 minutes at 0°
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationConcentration
  8. customgave a viscous brown oil which

Sources & evidence

ORD record
ord-faead79a1ff64b9ca375776ca93da693
Source dataset
uspto-grants-1988_09
Patent number
US04770690

Reaction notes

Loading…