Hydrochloric Acid → HCID 86590609, compound

HRID 1725583Notes

Reaction equation

HRID 1725583 reaction equation
C[O:2][C:3]1C=C(C=C[C:10]=1OCC1C=CC(OC)=CC=1)C=O.C[O-].[Na+].Cl.[NH:25]([CH:32]=[C:33]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)=[C:39]([O:53][CH3:54])[CH:38]=1)[C:34]#[N:35])[C:26]1C=CC=C[CH:27]=1>CS(C)=O.ClCCl.O>[CH3:54][O:53][C:39]1[CH:38]=[C:37]([CH:42]=[CH:41][C:40]=1[O:43][CH2:44][C:45]1[CH:46]=[CH:47][C:48]([O:51][CH3:52])=[CH:49][CH:50]=1)[CH2:36][C:33](=[CH:32][N:25]1[CH2:26][CH2:27][O:2][CH2:3][CH2:10]1)[C:34]#[N:35]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 27644923-Methoxy-4-[(4-methoxyphenyl)methoxy]benzaldehydeHCID 10942334Sodium MethoxideHCID 69006529HCID 69006529, compound

Product 1

HCID 86590609HCID 86590609, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-Methoxy-4-[(4-methoxybenzyl)oxy]benzaldehyde (20.0 g, 73.4 mmol) and 3-morpholinopropronitrile (Lancaster, 11.0 g, 77.1 mmol) were stirred in DMSO (15 mL) at 65 C until the mixture was homogeneous. The solution was cooled to 40 C and sodium methoxide (0.79 g, 14.7 mmol) was added. The mixture was stirred at 75 C for 15 minutes, then cooled to room temperature and diluted with dichloromethane (150 mL) and water (200 mL). 1N HCl (25 mL) was added and the two layers were seperated. The organics were combined and dried (magnesium sulfate), filtered and concentrated to a red oil (29.5 g, 73 mmol) that was used directly in the synthesis of 3-anilino-2-{3-methoxy-4-[(4-methoxybenzyl)oxy]benzyl}prop-2-enenitrile. 1H NMR (300 MHz, d6-DMSO): δ 7.38 (d, 2H), 7.03-6.95 (m,3H), 6.84 (t, J=13.5 Hz, 2H), 6.73 (d, J=8.2 Hz, 1H), 4.98 (s, 3H), 3.78 (s, 3H), 3.76 (s, 3H), 3.66-3.60 (m, 2H), 3.55-3.50 (m, 3H), 3.46-3.43 (m, 2H), 3.36 (s, 1H), 3.33-3.29 (m, 2H). MS (ES+, m/z)=395 (M+H).

Workup

  1. additionwas added
  2. customthe two layers were seperated
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-cff3f35122464fdb8079e68c06cecdaa
Source dataset
uspto-grants-2009_02
Patent number
US07491731B2

Reaction notes

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