Thionyl Chloride → HCID 21877602, compound

HRID 1862156Notes

Reaction equation

HRID 1862156 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18]O)(=[O:12])=[O:11].O=S(Cl)[Cl:22]>C(Cl)(Cl)Cl>[Cl:22][CH2:18][C:14]1[N:13]([S:10]([C:3]2[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=2[CH3:9])(=[O:12])=[O:11])[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21877558[1-(2,4,6-Trimethyl-benzenesulfonyl)-1H-pyrrol-2-yl]-methanol

Product 1

HCID 21877602HCID 21877602, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of [1-(2,4,6-Trimethyl-benzenesulfonyl)-1H-pyrrol-2-yl]-methanol (1.4 g, 5.0 mmol) in CHCl3 (25 ml) was cooled with an ice bath. SOCl2 (1.1 ml, 15 mmol) was added slowly. The solution was allowed to warm to rt, and held an additional 45 min. The solution was then concentrated under reduced pressure. 2-Chloromethyl-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrole was obtained as a brown solid (1.5 g, 100%). 1H NMR (CDCl3) δ 7.28 (dd, 1H, J=3.3, 1.7 Hz), 6.98 (s, 2H), 6.38-6.34 (m, 1H), 6.19 (t, 1H, J=3.4 Hz), 4.58 (s, 2H), 2.50 (s, 6H), 2.30 (s, 3H).

Workup

  1. concentrationThe solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-1f049f00fa6a46e1b712902362da6ee8
Source dataset
uspto-grants-2003_03
Patent number
US06534524B1

Reaction notes

Loading…