Benzoyl isocyanate → HCID 67399349, compound

HRID 711768Notes

Reaction equation

HRID 711768 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH:11]2[CH2:14][CH2:13][CH2:12]2)[C:3]=1[C:4]#[N:5].[C:15]([N:23]=[C:24]=[O:25])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCOCC1.CCOC(C)=O>[C:4]([C:3]1[C:6]([O:10][CH:11]2[CH2:12][CH2:13][CH2:14]2)=[CH:7][CH:8]=[CH:9][C:2]=1[NH:1][C:24]([NH:23][C:15](=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:25])#[N:5]

Participants

5

Reactant 2

HCID 78210Benzoyl isocyanateHCID 67400719HCID 67400719, compound

Product 1

HCID 67399349HCID 67399349, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-6-cyclobutoxybenzonitrile (example 162b) (30 mg, 0.16 mmol) in 1,4-dioxane (2 mL) was added benzoyl isocyanate (23 mg, 0.16 mmol). The reaction was stirred at rt under N2 for 19 hours. Upon completion, the reaction was diluted with EtOAc, washed with saturated NaHCO3 (2×), water, brine, dried over MgSO4, filtered and concentrated to provide N-(2-cyano-3-cyclobutoxyphenylcarbamoyl)benzamide (38 mg, 71%). 1H NMR (400 MHz, DMSO-d6) δ 1.64 (m, 1H), 1.81 (m, 2H), 2.05 (m, 1H), 2.42 (m, 2H), 4.71 (pent, J=7.1 Hz, 1H), 6.05 (d, J=8.2 Hz, 1H), 6.33 (d, J=8.3 Hz, 1H), 7.15 (t, J=8.5 Hz, 1H), 7.45 (m, 1H), 7.56 (m, 2H), 7.87 (m, 1H), 8.05 (m, 1H), 11.35 (s, 1H).

Workup

  1. washwashed with saturated NaHCO3 (2×), water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dd0e0e652b784dec83e9d54675bafaa5
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

Loading…