Veratrole → N-[2-[bis(1-methylethyl)amino]ethyl]-3,4-dimethoxy-N-(1-methylethyl)-benzenesulfonamide

HRID 2413999Notes

Reaction equation

HRID 2413999 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11](Cl)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1(OC)C(=CC=CC=1)OC.ClS(O)(=O)=O.[CH:30]([N:33]([CH:40]([CH3:42])[CH3:41])[CH2:34][CH2:35][NH:36][CH:37]([CH3:39])[CH3:38])([CH3:32])[CH3:31]>>[CH3:42][CH:40]([N:33]([CH:30]([CH3:32])[CH3:31])[CH2:34][CH2:35][N:36]([CH:37]([CH3:39])[CH3:38])[S:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:13])=[O:12])[CH3:41]

Participants

5

Reactant 4

HCID 7043VeratroleHCID 24638Chlorosulfonic acidHCID 667971,2-Ethanediamine, N,N,N'-tris(1-methylethyl)-HCID 27341833,4-Dimethoxybenzenesulfonyl chloride

Product 1

HCID 14096741N-[2-[bis(1-methylethyl)amino]ethyl]-3,4-dimethoxy-N-(1-methylethyl)-benzenesulfonamide

Procedure

3,4-Dimethoxybenzene sulfonyl chloride, prepared from veratrole and chlorosulfonic acid was reacted with N,N,N'-triisopropyl ethylene diamine following the procedure of Example 1. The reaction was worked up and the crude product chromatographed on alumina with ethyl acetate. The pure product was obtained, m.r. 69°-71° C.

Workup

  1. customthe crude product chromatographed on alumina with ethyl acetate
  2. customThe pure product was obtained
  3. custom69°-71° C.

Sources & evidence

ORD record
ord-4187c3dcec7a4b8b91d5168270a89606
Source dataset
uspto-grants-1988_01
Patent number
US04720580

Reaction notes

Loading…