Benzoyl isocyanate → HCID 67399349, compound

HRID 471632Notes

Reaction equation

HRID 471632 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 Na 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-d80455559c01408ea5b2673b74796d9f
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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