Thionyl Chloride → 4-tert-Butyl-N-[4-chloro-2-(chloro-pyridin-4-yl-methyl)-phenyl]-benzenesulfonamide

HRID 2079495Notes

Reaction equation

HRID 2079495 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[CH:22](O)[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O=S(Cl)[Cl:32]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[CH:22]([Cl:32])[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 586460384-tert-Butyl-N-[4-chloro-2-(hydroxy-pyridin-4-yl-methyl)-phenyl]-benzenesulfonamide

Product 1

HCID 594855024-tert-Butyl-N-[4-chloro-2-(chloro-pyridin-4-yl-methyl)-phenyl]-benzenesulfonamide

Conditions

Temperature
80 °C

Procedure

4-tert-Butyl-N-[4-chloro-2-(hydroxy-pyridin-4-yl-methyl)-phenyl]-benzenesulfonamide (1.1 g, 2.5 mmol) was dissolved in SOCl2 and heated at 80° C. overnight. Excess SOCl2 was removed by rotary evaporation. The residue suspended in 50 mL DCM was washed with saturated sodium bicarbonate solution (50 mL) and dried over MgSO4. Evaporation of solvent gave white crystalline solid. MS: (M+H)=450.

Workup

  1. customExcess SOCl2 was removed by rotary evaporation
  2. washwas washed with saturated sodium bicarbonate solution (50 mL)
  3. dry with materialdried over MgSO4
  4. customEvaporation of solvent
  5. customgave white crystalline solid

Sources & evidence

ORD record
ord-410e1da6702d48ffac7175cd0bc4b3ba
Source dataset
uspto-grants-2011_04
Patent number
US07932252B2

Reaction notes

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