Benzenecarbodithioic acid → HCID 17866106, compound

HRID 1297486Notes

Reaction equation

HRID 1297486 reaction equation
[C:1]([SH:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([CH3:17])=[CH2:16])=[CH:13][CH:12]=1>CCCCCC>[C:1]([S:9][C:15]([C:14]1[CH:18]=[CH:19][C:11]([Cl:10])=[CH:12][CH:13]=1)([CH3:17])[CH3:16])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67141Benzenecarbodithioic acidHCID 743814-Chloro-alpha-methylstyrene

Product 1

HCID 17866106HCID 17866106, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

Dithiobenzoic acid (6.3 g) and 4-chloro-a-methylstyrene (6 g) were combined and the mixture heated at 70° C. overnight. The residue was subjected to column chromatography (Kieselgel-60, 70-230 mesh, n-hexane as eluent) which gave the title compound as a purple solid (34.2% yield) m.p. 77-78° C. 1H-nmr (CDCl3) d (ppm): 1.97 (s, 6H, 2×CH3), 7.20-7.52 (m, 7H, ArH) and 7.86 (d, 2H, ArH). 13C-nmr (CDCl3) d (ppm): 28.4, 55.7, 126.5, 128.1, 131.9, 132.4, 142.8, 146.0. The signal due to C═S (d>220.0 ppm) was beyond the frequency range of the spectrum.

Sources & evidence

ORD record
ord-8d035779cd9d4770b3227a7495ad405e
Source dataset
uspto-grants-2007_07
Patent number
US07250479B2

Reaction notes

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