Triethylamine → N-(2,4,4-Trimethylpentan-2-yl)ethenesulfonamide

HRID 1272070Notes

Reaction equation

HRID 1272070 reaction equation
Cl[CH2:2][CH2:3][S:4](Cl)(=[O:6])=[O:5].[C:8]([NH2:16])([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:9].C(N(CC)CC)C>ClCCl>[CH3:9][C:8]([NH:16][S:4]([CH:3]=[CH2:2])(=[O:6])=[O:5])([CH3:10])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 61017tert-Octylamine

Product 1

HCID 17748074N-(2,4,4-Trimethylpentan-2-yl)ethenesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Chloro-1-ethane sulfonyl chloride (51.3 mL, 0.49 mol) in dichloromethane (400 mL) was added dropwise over 2 hours to a solution of tert-octylamine (236.3 mL, 1.47 mol) and triethylamine (68.3 mL, 0.49 mol) in dichloromethane (400 mL) at −18° C. The mixture temperature was maintained between −18° C. and −9° C. during the addition. The mixture was allowed to warm to ambient temperature over 1 hour then washed with 1N HCl (400 mL) and distilled water (2×200 mL). The organic layer was dried with MgSO4, filtered and concentrated in vacuo to give a pale yellow oil. The oil was dried under vacuum at 50° C. to give ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide, 96.0 g (90% yield) as a pale yellow oil.

Workup

  1. temperatureThe mixture temperature was maintained between −18° C. and −9° C. during the addition
  2. washthen washed with 1N HCl (400 mL)
  3. distillationdistilled water (2×200 mL)
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a pale yellow oil
  8. customThe oil was dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-9413b4ef83f54cb4b77ef98a5526482b
Source dataset
uspto-grants-2007_04
Patent number
US07208506B2

Reaction notes

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