Sulfur Dioxide → HCID 18324212, compound

HRID 1251698Notes

Reaction equation

C[N:2]1[C:10]2[C:5](=CC=CC=2)C=C1.[Li][C:12]([CH3:15])([CH3:14])[CH3:13].[S:16](=[O:18])=[O:17].C1C(=O)N([Cl:26])C(=O)C1.[CH2:27]1[CH2:31]OC[CH2:28]1>>[CH3:5][C:10]1([S:16]([Cl:26])(=[O:18])=[O:17])[CH:15]=[C:12]2[C:14]([CH:28]=[CH:27][CH:31]=[CH:13]2)=[N:2]1

Participants

Reactant 5

HCID 1119Sulfur Dioxide

HCID 8028Tetrahydrofuran

HCID 117811-Methylindole

HCID 31398Chlorosuccinimide

HCID 178418306HCID 178418306, compound

Product 1

HCID 18324212HCID 18324212, compound

Procedure

2-Methylindole-2-sulfonyl chloride was prepared by the method of Example 34 with 1-methylindole (7.8 mmols, 1.0 ml), t-BuLi (1.7 m, 9.4 mmols, 5.5 ml), sulfur dioxide, NCS (8.6 mmols, 1.2 g) and THF (15 ml). Flash chromatography (2% ethyl acetate/hexanes) provided 0.66 g (36%) of a yellow solid.

Sources & evidence

ORD record: ord-645074c2c7c949aebc82ddbb86c156ab
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06342610B2

Reaction notes

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