Hydrochloric Acid → N-(2-Hydroxyethyl)-4-methoxy-N,2,6-trimethylbenzenesulfonamide

HRID 222524Notes

Reaction equation

HRID 222524 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl[S:12]([OH:15])(=O)=[O:13].[Cl-].[Na+].[CH3:18][NH:19][CH:20](O)[CH3:21].Cl.[OH2:24]>ClCCl>[OH:24][CH2:21][CH2:20][N:19]([CH3:18])[S:12]([C:7]1[C:6]([CH3:8])=[CH:5][C:4]([O:9][CH3:10])=[CH:3][C:2]=1[CH3:1])(=[O:15])=[O:13]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 962Water2×HCID 5234Sodium ChlorideHCID 24638Chlorosulfonic acidHCID 701263,5-DimethylanisoleHCID 5247031N-Methylaminoethanol

Product 1

HCID 51712110N-(2-Hydroxyethyl)-4-methoxy-N,2,6-trimethylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-7 °C

Procedure

10.00 kg (73.42 mol) of 3,5-dimethylanisol (A) were dissolved in 35.0 L of dichloromethane. After cooling to −15±5° C. a solution of 17.46 kg (149.86 mol) of chlorosulphonic acid in 20.0 L dichloromethane was metered in and the mixture was stirred for approx. another 30 minutes at −15±5° C. Then the reaction mixture was metered into a solution of 15.0 kg sodium chloride in 85.0 L of water that had been cooled to −7±5° C., and diluted with 15.0 L of dichloromethane. The organic phase was separated off, diluted with 15.0 L of dichloromethane and washed with 30.0 L of sodium hydrogen carbonate solution (5%). After separation of the organic phase once again and dilution with 10 L of dichloromethane, a solution of 11.58 kg (154.20 mol) N-methylaminoethanol in 10.0 L of dichloromethane was slowly metered in at 10±5° C. After the reaction had ended 45.0 L of HCl (3%) and 5.0 L of water were added. The organic phase was separated off, diluted with 10.0 L dichloromethane and the solvent was totally eliminated from the product (C) in vacuo.

Workup

  1. customThe organic phase was separated off
  2. additiondiluted with 15.0 L of dichloromethane
  3. washwashed with 30.0 L of sodium hydrogen carbonate solution (5%)
  4. customAfter separation of the organic phase once again
  5. customwas slowly metered in at 10±5° C
  6. additionwere added
  7. customThe organic phase was separated off
  8. additiondiluted with 10.0 L dichloromethane

Sources & evidence

ORD record
ord-9f1f5c869ec84a169535a776eb208804
Source dataset
uspto-grants-2012_06
Patent number
US08207335B2

Reaction notes

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