2-Propanethiol → 5-Nitro-2-(propane-2-sulfonyl)benzonitrile

HRID 735506Notes

Reaction equation

HRID 735506 reaction equation
[CH2:1]([S:3]([C:6]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:7]=1[C:8]#[N:9])(=[O:5])=[O:4])[CH3:2].F[C:18]1C=CC([N+]([O-])=O)=CC=1C#N.CC(S)C.C1C=C(Cl)C=C(C(OO)=O)C=1>>[CH:1]([S:3]([C:6]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:7]=1[C:8]#[N:9])(=[O:4])=[O:5])([CH3:18])[CH3:2]

Participants

5

Reactant 4

HCID 63642-PropanethiolHCID 70297m-Chloroperbenzoic acidHCID 5194172-Fluoro-5-nitrobenzonitrileHCID 574481822-(Ethanesulfonyl)-5-nitrobenzonitrile

Product 1

HCID 574482065-Nitro-2-(propane-2-sulfonyl)benzonitrileYield 91%

Procedure

Using a procedure analogous to that used to prepare 6A, 2-fluoro-5-nitrobenzonitrile (2.50 g, 15.6 mmol) was reacted with isopropylthiol and oxidized with mCPBA to afford 9A (3.04 g, 91%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.40 (d, J=7.03 Hz, 6 H), 3.55-3.76 (m, 1 H), 8.38 (d, J=8.35 Hz, 1 H), 8.63 (dd, J=8.79, 2.20 Hz, 1 H), 8.74 (d, J=2.64 Hz, 1 H).

Sources & evidence

ORD record
ord-6857cb8dcdde477b8701b4b5980a565f
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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