Lawesson's reagent → HCID 86642943, compound

HRID 1811031Notes

Reaction equation

HRID 1811031 reaction equation
[Br:1][C:2]1[C:3]([CH3:18])=[C:4]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[CH:5]=[CH:6][CH:7]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:28]2)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([CH3:18])=[C:4]([NH:8][C:9](=[S:28])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 66606524HCID 66606524, compound

Product 1

HCID 86642943HCID 86642943, compoundYield 150%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Step 2 A mixture of N-(3-bromo-2-methylphenyl)-2-fluorobenzamide (2.00 g, 6.49 mmol) and 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide (Lawesson reagent, 1.575 g, 3.89 mmol) in toluene (25 mL) was heated at reflux. After 3.5 h, the solution was cooled to rt and concentrated to provide a dark yellow solid. This was purified by column chromatography (eluting with a gradient from 95:5 to 90:10 hexane-EtOAc) to provide N-(3-bromo-2-methylphenyl)-2-fluorobenzothioamide as a yellow solid (1.892 g, 90%). 1H NMR (400 MHz, chloroform-d) δ 9.18 (1 H, d, J=7.7 Hz), 8.23 (1 H, td, J=8.0, 1.8 Hz), 7.60 (1 H, d, J=7.9 Hz), 7.45-7.52 (1 H, m), 7.43 (1 H, d, J=7.7 Hz), 7.23-7.30 (1 H, m), 7.11-7.21 (2 H, m), 2.41 (3 H, s). Mass spectrum m/z 324, 326 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. concentrationconcentrated
  4. customto provide a dark yellow solid
  5. customThis was purified by column chromatography (
  6. washeluting with a gradient from 95:5 to 90:10 hexane-EtOAc)

Sources & evidence

ORD record
ord-0a20dc7816ff4dccba852dc909e2c04f
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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