Hydrochloric Acid → HCID 51348808, compound

HRID 924849Notes

Reaction equation

HRID 924849 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.[OH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][C:18]=1[O:25][CH3:26].[NH2:27][C:28]([NH2:30])=[O:29].Cl>CCO>[OH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]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:19][C:18]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 1183VanillinHCID 99482-Phenylacetophenone

Product 1

HCID 51348808HCID 51348808, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 1,2-diphenylethanone (392 mg, 2.0 mmol), 4-hydroxy-3-methoxybenzaldehyde (274 mg, 1.8 mmol) and urea (324 mg, 5.4 mmol) in EtOH (40 mL) was added concentrated HCl (0.17 mL). The mixture was stirred at 85° C. for 3 days. The volatiles were removed under reduced pressure and the residue was diluted with water (50 mL), extracted with ethyl acetate (100 mL×2), washed with saturated aqueous NaHCO3 (50 mL×2), dried over Na2SO4, concentrated (standard aqueous/EtOAc workup) and purified by silica gel column chromatography (PE:EA=1:1) to afford Compound 87 as an off-white power (100 mg, 15%). 1H NMR (DMSO-d6 500 MHz): δ 8.94 (s, 1H), 8.58 (s, 1H), 7.36 (s, 1H), 7.53 (s, 1H), 7.40 (s, 3H), 7.34 (s, 3H), 7.10 (d, J=5.2 Hz, 1H), 7.20-7.25 (m, 5H), 6.99 (t, J=18 Hz, 3H), 6.90 (s, 1H), 6.80 (t, J=7.0 Hz, 3H), 6.74 (d, J=8.0 Hz, 1H), 4.99 (d, J=2.5 Hz, 1H); MS (ESI): m/z 373.0 [M+1]+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionthe residue was diluted with water (50 mL)
  3. extractionextracted with ethyl acetate (100 mL×2)
  4. washwashed with saturated aqueous NaHCO3 (50 mL×2)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated (standard aqueous/EtOAc workup)
  7. custompurified by silica gel column chromatography (PE:EA=1:1)

Sources & evidence

ORD record
ord-dd9ad24e721040d0b845212c0f4efa67
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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