2-Propanethiol → 2-[(1-Methylethyl)thio]-5-nitrobenzaldehyde

HRID 1893135Notes

Reaction equation

Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:19][CH:20]([SH:22])[CH3:21]>CN(C=O)C>[CH:20]([S:22][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5])([CH3:21])[CH3:19]

Participants

Conditions

Temperature: 55 °C

Procedure

2-chloro-5-nitrobenzaldehyde (2.99 g, 16.1 mmol), potassium carbonate (2.45 g, 17.7 mmol) and propane-2-thiol (1.35 g, 17.7 mmol) were dissolved in 10.0 ml, DMF in a 50 mL, round-bottomed flask under dry nitrogen, topped with a reflux condenser. The reaction mixture was heated to 55° C. for 24 h. After cooling the mixture was added to 150 mL of saturated potassium carbonate solution. The yellow-brown solid was filtered, washed with water and further purified by chromatography on silica gel using 10:1 petroleum ether 60-80 and ether as eluent. Yield: 1.81 g, 50%, yellow solid. 1H NMR (200 MHz, CDCl3): δ 1.46 (d, J=6.9 Hz, 6H), 3.67 (septet, J=6.9 Hz, 1H), 7.55 (d, J=8.7 Hz, 1H), 8.32 (dd, J=2.5, 8.7 Hz, 1H), 8.66 (d, J=2.5 Hz, 1H), 10.3 (s, 1H) ppm. 13C NMR (50 MHz, CDCl3): δ 22.5, 36.6, 127.2, 127.4, 127.9, 133.4, 144.7, 150.8, 189.1.

Workup

customtopped with a reflux condenser
temperatureAfter cooling the mixture
filtrationThe yellow-brown solid was filtered
washwashed with water
customfurther purified by chromatography on silica gel using 10:1 petroleum ether 60-80 and ether as eluent

Sources & evidence

ORD record: ord-3df7686a834c4be899a78fb69d9448ae
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513151B2

Reaction notes

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