Hydrochloric Acid → 4-(2-Bromoethyl)-N-(3-methyl-2-pyridinyl)benzenesulfonamide

HRID 1464167Notes

Reaction equation

[CH3:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[Br:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.Cl>ClCCl>[Br:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([S:18]([NH:8][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)(=[O:20])=[O:19])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 35 °C

Procedure

3-Methyl-2-pyridinamine (431 g, 4.0 mol) was dissolved in dichloromethane (700 ml) and 4-(2-bromoethyl)benzenesulfonyl chloride (340 g, 1.33 mol) was added at room temperature. After 1 h at 20° C., the solution was heated to 35° C. for 2 h. Excess dilute hydrochloric acid was added and the phases separated. After washing once with water, the organic phase was dried with MgSO4 and treated with decolorizing carbon. The solvent was evaporated and warm methanol added to the residue, which crystallized. The material was collected and recrystallized from toluene. Yield 178 g. A further crop of 36 g was obtained by workup of the mother liquor. Total yield 45%.

Workup

customthe phases separated
washAfter washing once with water
dry with materialthe organic phase was dried with MgSO4
additiontreated with decolorizing carbon
customThe solvent was evaporated
temperaturewarm methanol
additionadded to the residue, which
customcrystallized
customThe material was collected
customrecrystallized from toluene
customA further crop of 36 g was obtained by workup of the mother liquor

Sources & evidence

ORD record: ord-6ab5598bc519477e8a2595e379016bc1
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05302718

Reaction notes

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