Benzoyl isothiocyanate → Ethyl 6-(3-benzoyl-thioureido)-nicotinate

HRID 6877

Reaction equation

HRID 6877 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[C:13]([N:21]=[C:22]=[S:23])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC(C)=O>[C:13]([NH:21][C:22](=[S:23])[NH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 235927Ethyl 6-Aminonicotinate

Product 1

HCID 86591884Ethyl 6-(3-benzoyl-thioureido)-nicotinateYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of ethyl 6-amino-nicotinate (830 mg, 5 mmol) and benzoyl isothiocyanate (830 mg, 5.1 mmol) in acetone was refluxed for 2 h. The mixture was concentrated to thin slurry and methanol was added. The solid was filtered, washed with methanol and dried to afford ethyl 6-(3-benzoyl-thioureido)-nicotinate (1.35 g, 82%). 1H NMR (CDCl3) δ 13.34 (s, 1 H), 9.04 (m, 3 H), 8.38 (s, 1 H), 7.93 (m, 2 H), 7.66 (m, 3 H), 4.42 (q, 2 H, J=7.6 Hz), 1.41(t, 3 H, J=7.6 Hz).

Workup

  1. concentrationThe mixture was concentrated to thin slurry and methanol
  2. additionwas added
  3. filtrationThe solid was filtered
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-446464081e0447db9f4ca083cb4217ae
Source dataset
uspto-grants-2006_08
Patent number
US07084160B2

Linked notes

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