Thionyl Chloride → HCID 21877602, compound

HRID 724427Notes

Reaction equation

HRID 724427 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-46ce0a05316945bcbecec2c17f16dd9a
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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