Triethylamine → HCID 54269131, compound

HRID 1040800Notes

Reaction equation

HRID 1040800 reaction equation
[CH3:1][C:2]([NH2:6])([CH3:5])[CH2:3][NH2:4].[S:7](Cl)([CH3:10])(=[O:9])=[O:8].C(N(CC)CC)C>C(Cl)Cl>[NH2:6][C:2]([CH3:5])([CH3:1])[CH2:3][NH:4][S:7]([CH3:10])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131282-MethylpropylenediamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 54269131HCID 54269131, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-propane-1,2-diamine (2.00 g, 22.7 mmol, 2.38 mL, 1.1 eq.) was placed in CH2Cl2 (100 mL). Mesyl chloride (2.35 g, 20.7 mmol, 1.59 mL, 1.0 eq.) was added over a period of five minutes followed by triethylamine (6.27 g, 62.1 mmol, 8.71 mL, 3.0 eq.). The reaction was stirred for 30 minutes and then concentrated under reduced pressure. Purification by basic alumina chromatography using a gradient of 0-15% MeOH/CH2Cl2 as the eluting solvent to obtain N-(2-amino-2-methyl-propyl)-methanesulfonamide as a white solid (1.15 g, 33%). LCMS (m/e) 167 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 2.98 (s, 3H), 2.95 (s, 2H), 1.17 (s, 3H), 1.16 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification by basic alumina chromatography

Sources & evidence

ORD record
ord-b5a9e663b16645eab38624fe3bcf1d65
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…