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

HRID 1378347Notes

Reaction equation

HRID 1378347 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].[I:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([NH:19][C:20]1[C:25]([O:26][CH3:27])=[N:24][C:23]([CH3:28])=[CH:22][N:21]=1)(=[O:18])=[O:17].C(N(CC)CC)C.Cl>ClCCl.N1C=CC=CC=1>[I:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([N:19]([C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3])[C:20]1[C:25]([O:26][CH3:27])=[N:24][C:23]([CH3:28])=[CH:22][N:21]=1)(=[O:17])=[O:18]

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 was added dropwise to a stirred solution of 2-iodo- N-(3-methoxy-5-methylpyrazin-2-yl)benzenesulphonamide (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 2M hydrochloric acid (20 ml) was added. The organic layer was separated, washed with water (20 ml) and saturated sodium chloride solution and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetateexane (1:4 v/v), to give 2-iodo- N-(isobutoxycarbonyl)- N-(3-methoxy-5-methylpyrazin-2-yl)benzenesulphonamide (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), (dd, 1H), 8.35 (dd, 1H). 4.0 (s, 3H), 7.4 (dt, 1H), 7.7 (dr, 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
  3. dry with materialdried (MgSO4)
  4. customVolatile material was removed by evaporation
  5. customthe residue was purified by flash chromatography
  6. washeluting with ethyl acetateexane (1:4 v/v)

Sources & evidence

ORD record
ord-ddb9246c900548fcac02633eddf9f846
Source dataset
uspto-grants-1997_09
Patent number
US05668137

Reaction notes

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