Hydrogen Bromide → 2-(Pyridin-2-yl)benzene-1-sulfonamide

HRID 35492Notes

Reaction equation

HRID 35492 reaction equation
CC([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)(=[O:8])=[O:7])(C)C.Br>CO>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[S:6]([NH2:5])(=[O:7])=[O:8]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 13370585N-tert-Butyl-2-(pyridin-2-yl)benzene-1-sulfonamide

Product 1

HCID 133705862-(Pyridin-2-yl)benzene-1-sulfonamideYield 50.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 14.8 g of the sulfonamide from Example 1 and 10 ml of 48% hydrobromic acid in 100 ml of methanol was heated at 40°-45° for 16 hours, concentrated, and neutralized with aqueous sodium bicarbonate. The solid was filtered, washed with ice-water, and air-dried to afford 6.0 g of product, m.p. 186°-190°. NMR(CDCl3 /DMSO-d6)δ: 7.5 (m, 7), 8.1 (m, 2), 8.6 (d, 1). IR(Nujol) 3300, 3260 cm-1. m/e M+ 234.

Workup

  1. concentrationconcentrated
  2. filtrationThe solid was filtered
  3. washwashed with ice-water
  4. customair-dried

Sources & evidence

ORD record
ord-9a5ee1ae29254eaaba9eec30c783012a
Source dataset
uspto-grants-1988_08
Patent number
US04767445

Reaction notes

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