Thionyl Chloride → HCID 21877602, compound

HRID 2181552Notes

Reaction equation

HRID 2181552 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-85543303496d49eea2dff053f814217d
Source dataset
uspto-grants-2005_05
Patent number
US06891044B2

Reaction notes

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