Hydrochloric Acid → N-(1,1,3,3-tetramethyl-butyl)-methanesulfonamide

HRID 1272071

Reaction equation

HRID 1272071 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([NH2:14])([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:8])[CH3:7].C(N(CC)CC)C.Cl>ClCCl>[CH3:7][C:6]([NH:14][S:2]([CH3:1])(=[O:4])=[O:3])([CH3:8])[CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 61017tert-Octylamine

Product 1

HCID 19681856N-(1,1,3,3-tetramethyl-butyl)-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (46 mL, 0.6 mol) in dichloromethane (100 mL) was added dropwise over 45 minutes to a solution of tert-octylamine (80 mL, 0.5 mol) and triethylamine (84 mL, 0.6 mol) in dichloromethane (400 mL) at 0° C. The mixture was stirred for a further 1 hour at room temperature then 1M HCl (1 L) was added in one portion. The mixture was extracted with dichloromethane (2×1 L). The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford N-(1,1,3,3-tetramethyl-butyl)-methanesulfonamide as a yellow oil (100.8g, 97%).

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×1 L)
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca3f3f3ce4db4450a9f2720c9c0de87e
Source dataset
uspto-grants-2007_04
Patent number
US07208506B2

Linked notes

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