Allyl Mercaptan → 4-Allylsulfanylmethyl-2,2-dimethyl-6-thiophen-3-yl-1,2-dihydroquinoline

HRID 25797

Reaction equation

[CH3:1][C:2]1([CH3:18])[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)[CH:8]=2)[NH:3]1.C1C(=O)N(Br)C(=O)C1.[CH2:27]([SH:30])[CH:28]=[CH2:29]>>[CH2:27]([S:30][CH2:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)[CH:8]=2)[NH:3][C:2]([CH3:18])([CH3:1])[CH:11]=1)[CH:28]=[CH2:29]

Participants

Reactant 3

HCID 13367Allyl Mercaptan

HCID 67184N-bromobutanimide

HCID 225665322,2,4-Trimethyl-6-thiophen-3-yl-1,2-dihydroquinoline

Product 1

HCID 225665344-Allylsulfanylmethyl-2,2-dimethyl-6-thiophen-3-yl-1,2-dihydroquinoline

Procedure

2,2,4-Trimethyl-6-thiophen-3-yl-1,2-dihydroquinoline was brominated with NBS using the procedure described in Example 1 and then coupled with allyl mercaptan using the procedure described in Example 2 to provide 22 mg of the title compound as a oil.

Sources & evidence

ORD record: ord-2ae737324b1e4979a5f2376838cc0e72
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858627B2

Linked notes

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