Hydrochloric Acid → HCID 56961406, compound

HRID 924858Notes

Reaction equation

HRID 924858 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[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([CH:25]=1)[C:23]#[N:24])=O.[NH2:27][C:28]([NH2:30])=[O:29].Cl>CCO>[OH:26][C:21]1[CH:20]=[CH:19][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][C:22]=1[C:23]#[N:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 221125485-Formyl-2-hydroxybenzonitrile2×

Product 1

HCID 56961406HCID 56961406, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1,2-diphenylethanone (720 mg, 3.67 mmol), 5-formyl-2-hydroxybenzonitrile (Intermediate 47a) (450 mg, 3.06 mmol) and urea (551 mg, 9.18 mmol) in EtOH (23 mL) was added concentrated HCl (0.9 mL). The mixture was stirred at 90° C. for 40 h. Followed standard aqueous workup procedure and recrystallized from EA (6 mL), then further purified by prep-HPLC to afford Compound 96 as a white power (36 mg, 3%). 1H NMR (MeOH-d4 500 MHz): δ 7.50 (t, J=7.5 Hz, 1H), 7.42 (d, J=2.0 Hz, 1H), 7.25 (s, 5H), 7.05 (t, J=2.5 Hz, 3H), 6.93 (d, J=8.5 Hz, 1H), 6.85 (t, J=4.0 Hz, 2H), 5.30 (s, 1H); MS (ESI): m/z 368.1 [M+1]+.

Workup

  1. customrecrystallized from EA (6 mL)
  2. customfurther purified by prep-HPLC

Sources & evidence

ORD record
ord-77238a0092bf4ce286c5d168f33f1579
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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