3-Pyridyl isothiocyanate → HCID 178493489, compound

HRID 1178702Notes

Reaction equation

HRID 1178702 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][CH3:19])[C:4]=1[CH2:5][S:6][C:7](=[NH:11])[CH2:8][C:9]#[N:10].[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]=[C:27]=[S:28])[CH:21]=1>C(OCC)(=O)C>[CH3:19][O:18][C:12]1[CH:13]=[C:14]([O:16][CH3:17])[CH:15]=[C:3]([O:2][CH3:1])[C:4]=1[CH2:5][S:6][C:7](=[NH:11])[C:8]([C:9]#[N:10])=[C:27]([SH:28])[NH:26][C:22]1[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 27372423-Pyridyl isothiocyanateHCID 69515586(2,4,6-Trimethoxyphenyl)methyl 2-cyanoethanimidothioate

Product 1

HCID 178493489HCID 178493489, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

To compound 11 (6.76 g, 24.1 mmol) in ethyl acetate (18 mL) is added 3-pyridylisothiocyanate (3.9 ml-, 36.2 mmol) at room temperature. The reaction is then heated to 60° C. and stirred for 4 hours. More ethyl acetate is added (12 mL) and the reaction is stirred for an additional 4 hours. The reaction is cooled to room temperature and filtered. The solids are washed with ethyl ether twice and with methanol once. The solids are further dried in vacuo to obtain compound 12 (5.88 g, 59%). 1H NMR (d6 DMSO): δ 10.12 (1H, br. s), 8.46 (1H, d, J=2.4 Hz), 8.36 (1H, d, J=5.2 Hz), 7.71 (1H, d, J=9.0 Hz), 7.37 (1H, dd, J=9.0, 5.2 Hz), 6.27 (2H, s), 4.25 (2H, s), 3.81 (6H, s), 3.77 (3H, s).

Workup

  1. stirringthe reaction is stirred for an additional 4 hours
  2. temperatureThe reaction is cooled to room temperature
  3. filtrationfiltered
  4. washThe solids are washed with ethyl ether twice
  5. customThe solids are further dried in vacuo

Sources & evidence

ORD record
ord-31acc6eb6d2c441c85721d86ea8a2734
Source dataset
uspto-grants-2007_10
Patent number
US07276602B2

Reaction notes

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