tert-Butyl mercaptan → HCID 57842722, compound

HRID 735511Notes

Reaction equation

C([S:3]([C:6]1[CH:13]=CC([N+]([O-])=O)=C[C:7]=1C#N)(=[O:5])=[O:4])C.F[C:18]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:19]=1[C:20]#[N:21].[CH3:29]C(S)(C)C.C1C=C(Cl)C=C(C(OO)=O)C=1>>[C:6]([S:3]([C:18]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:19]=1[C:20]#[N:21])(=[O:5])=[O:4])([CH3:13])([CH3:29])[CH3:7]

Participants

Reactant 4

HCID 6387tert-Butyl mercaptan

HCID 70297m-Chloroperbenzoic acid

HCID 5194172-Fluoro-5-nitrobenzonitrile

HCID 574481822-(Ethanesulfonyl)-5-nitrobenzonitrile

Product 1

HCID 57842722HCID 57842722, compoundYield 88%

Procedure

Using a procedure analogous to that used to prepare 6A, 2-fluoro-5-nitrobenzonitrile (2.50 g, 15.6 mmol) was reacted with tert-butylthiol and oxidized with mCPBA to afford 10A (3.14 g, 88%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 9 H), 7.88 (d, J=8.79 Hz, 1 H), 8.37 (dd, J=8.35, 2.64 Hz, 1 H), 8.55 (d, J=2.64 Hz, 1 H).

Sources & evidence

ORD record: ord-366e55aa010640e893c848d56b0916f7
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

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