Hydrochloric Acid → N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide

HRID 2287406Notes

Reaction equation

HRID 2287406 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].[CH3:9][O:10][C:11]1[C:12]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[I:28])(=[O:21])=[O:20])=[N:13][CH:14]=[C:15]([CH3:17])[N:16]=1.C(N(CC)CC)C.Cl>ClCCl.N1C=CC=CC=1>[CH2:5]([O:4][C:2]([N:18]([C:12]1[C:11]([O:10][CH3:9])=[N:16][C:15]([CH3:17])=[CH:14][N:13]=1)[S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[I:28])(=[O:21])=[O:20])=[O:3])[CH:6]([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 10173047N-(3-Methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide

Product 1

HCID 18704832N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Isobutyl chloroformate (0.58 ml) was added dropwise to a stirred solution of N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide (1.65 g), triethylamine (0.57 ml) and pyridine (0.16 ml) in dichloromethane (30 ml) under an atmosphere of argon. The mixture was stirred for 2 hours and then 2H hydrochloric acid (20 ml) was added. The organic layer was separated, washed with water (20 ml) and saturated sodium chloride solution (20 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:4 v/v), to give N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide (2.0 g) as a gum; 1H NMR (d6 -DMSO): 0.7 (d,2H), 1.6-1.8 (m,1H), 2.5 (s,3H), 3.9 (d,2H), 4.0 (s,3H), T.4 (dt,1H), 7.7 (dt,1H), 8.15 (s,1H), 8.2 (dd,1H), 8.35 (dd,1H).

Workup

  1. customThe organic layer was separated
  2. washwashed with water (20 ml) and saturated sodium chloride solution (20 ml)
  3. dry with materialdried (MgSO4)
  4. customVolatile material was removed by evaporation
  5. customthe residue was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1:4 v/v)

Sources & evidence

ORD record
ord-77b3d3e4ce21445dbe31bc0a33274d64
Source dataset
uspto-grants-2000_07
Patent number
US06083951

Reaction notes

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