6,6-Dimethyl-3-(methylthio)-4-oxo-4,5,6,7-tetrahydrobenzo(c)thiophene-1-carbonitrile → 1-Cyano-6,6-dimethyl-3-isopropyl-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one

HRID 1385284Notes

Reaction equation

HRID 1385284 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[C:6]([C:8]1[S:9][C:10](SC)=[C:11]2[C:16](=[O:17])[CH2:15][C:14]([CH3:19])([CH3:18])[CH2:13][C:12]=12)#[N:7]>>[C:6]([C:8]1[S:9][C:10]([CH:1]([CH3:3])[CH3:2])=[C:11]2[C:16](=[O:17])[CH2:15][C:14]([CH3:19])([CH3:18])[CH2:13][C:12]=12)#[N:7]

Participants

3

Reactant 2

HCID 27787536,6-Dimethyl-3-(methylthio)-4-oxo-4,5,6,7-tetrahydrobenzo(c)thiophene-1-carbonitrileHCID 178418918HCID 178418918, compound

Product 1

HCID 211845201-Cyano-6,6-dimethyl-3-isopropyl-4,5,6,7-tetrahydrobenzo[c]thiophen-4-oneYield 36%

Procedure

In the same way as described in Example 6, Step 1, using isopropylmagnesium chloride and 1-cyano-6,6-dimethyl-3-methylthio-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one, the title compound (1.2 g, 36%) was isolated as a colourless solid. mp 59-60° C. Found: C, 68.08; H, 6.97; N, 5.48%. C14H17NOS requires: C, 67.98; H, 6.93; N, 5.66%. 1HNMR (360 MHz, CDCl3) δ 1.08 (6H, s), 1.32 (6H, d, J=6.7 Hz), 2.43 (2H, s), 2.85 (2H, s), 4.24 (1H, heptet, J=6.7 Hz).

Sources & evidence

ORD record
ord-e08f1d539a6d442883cdd0dd6f2dd21e
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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