Urea → HCID 56961407, compound

HRID 401069Notes

Reaction equation

HRID 401069 reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:16]([C:18]1[C:19]([OH:26])=[C:20]([CH:23]=[CH:24][CH:25]=1)[C:21]#[N:22])=O.[NH2:27][C:28]([NH2:30])=[O:29]>CC(O)=O>[OH:26][C:19]1[C:18]([CH:16]2[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[NH:30][C:28](=[O:29])[NH:27]2)=[CH:25][CH:24]=[CH:23][C:20]=1[C:21]#[N:22]

Participants

5

Reactant 3

HCID 1176UreaHCID 99482-PhenylacetophenoneHCID 205546503-Formyl-2-hydroxybenzonitrile2×

Product 1

HCID 56961407HCID 56961407, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1,2-diphenylethanone (1.6 g, 8.16 mmol), and 3-formyl-2-hydroxybenzonitrile (Intermediate 47b) (1.0 g, 6.80 mmol) in AcOH (5 mL) was added urea (1.2 g, 20.4 mmol). The mixture was stirred at 120° C. under microwave for 3 h. The volatiles were removed under reduced pressure and standard aqueous workup procedure was followed. The crude was recrystallized by EA (10 mL) to afford Compound 94 as a white power (436 mg, 26%). 1H NMR (DMSO-d6 500 MHz): δ 8.10 (s, 1H), 7.79 (d, J=2.5 Hz, 1H), 7.75 (d, J=2.0 Hz, 1H), 7.58 (d, J=7.5 Hz, 3H), 7.30-7.36 (m, 3H), 7.18 (s, 1H), 7.02 (d, J=6.0 Hz, 3H), 6.78 (d, J=6.0 Hz, 2H), 4.44 (d, J=2.0 Hz, 1H), 4.14 (s, 1H); MS (ESI): m/z 368.1 [M+1]+.

Workup

  1. customThe volatiles were removed under reduced pressure and standard aqueous workup procedure
  2. customThe crude was recrystallized by EA (10 mL)

Sources & evidence

ORD record
ord-cbafa899a75c431591f53b58a6ff9326
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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