Benzoyl isothiocyanate → HCID 90404478, compound

HRID 924249Notes

Reaction equation

HRID 924249 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][CH2:10][CH3:11])=[C:6]([CH:8]=1)[NH2:7].[C:12]([N:20]=[C:21]=[S:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(C)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][CH2:10][CH3:11])=[C:6]([NH:7][C:21]([NH:20][C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[S:22])[CH:8]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 53800826HCID 53800826, compound

Product 1

HCID 90404478HCID 90404478, compoundYield 113.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To 5-methyl-2-propylaniline (CA26) (1.38 g, 9.22 mmol) and benzoyl isothiocyanate (1.24 mL, 9.22 mmol) was added acetone (13 mL). The reaction was heated at 60° C. for 4 h. The reaction was cooled and concentrated. The resulting oil was dried in a vacuum oven overnight providing the title compound as a brown oil (3.26 g, 100%): 1H NMR (400 MHz, CDCl3) δ 12.20 (s, 1H), 9.15 (s, 1H), 7.92 (dt, J=8.5, 1.7 Hz, 2H), 7.71-7.60 (m, 1H), 7.55 (m, 3H), 7.18 (d, J=7.8 Hz, 1H), 7.09 (dd, J=7.8, 1.1 Hz, 1H), 2.66-2.55 (m, 2H), 2.36 (s, 3H), 1.72-1.57 (m, 2H), 0.97 (t, J=7.3 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 179.64, 166.90, 136.22, 135.72, 134.57, 133.74, 131.68, 129.79, 129.22, 128.64, 127.55, 127.24, 33.28, 23.58, 21.01, 13.98; ESIMS m/z 313 ([M+H]+).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customThe resulting oil was dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-fb7bc6ef7c1a41229c2e4acb9dfb19db
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

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