4-Hydroxybenzaldehyde → HCID 86651919, compound

HRID 417781Notes

Reaction equation

HRID 417781 reaction equation
O[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13]([S:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=1)=[S:14])[CH3:11].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:10]([O:12][C:13]([S:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([C:31]([O:33][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[O:32])=[CH:34][CH:35]=1)=[S:14])[CH3:11]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10868DicyclohexylcarbodiimideHCID 86651920HCID 86651920, compound

Product 1

HCID 86651919HCID 86651919, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

p-Hydroxybenzaldehyde (0.37 g, 3.0 mmol), 8 (1.2 g, 3.0 mmol), and DMAP (0.04 g, 0.3 mmol) were dissolved in 300 mL of CH2Cl2. DCC (1.24 g, 6.0 mmol) was added to reaction flask which was stirred at room temperature for three days. The solvent was removed under reduced pressure, and the residue purified using column chromatography (CH2Cl2:EtOH, 10:0.05). The product was then recrystallized from ethanol. Yield 0.3 g (20%). 1HNMR: δH (CDCl3; 300 MHz): 1.24-1.52 (15 H, m, CH2/O—CH2—CH3), 1.69 (2 H, m, S—CH2—CH2), 1.81 (2 H, m, O—CH2—CH2), 3.11 (2 H, t, 3J=7.3 Hz, SCH2), 4.02 (2 H, t, 3J=6.5 Hz, O—CH2), 4.65 (2 H, q, 3J=7.1 Hz, O—CH2—CH3), 6.99 (2 H, d, 3J=8.9 Hz, Ar—H), 7.40 (2 H, d, 3J=8.5 Hz, Ar—H), 7.96 (2 H, d, 3J=8.6 Hz, Ar—H), 8.14 (2 H, d, 3J=8.9 Hz, Ar—H), 10.0 (1 H, s, COH). 13C NMR: δC (CDCl3; 75 MHz): 13.8, 25.9, 28.1, 28.3, 28.8, 29.1, 29.3, 29.4, 35.9, 68.4, 69.7, 114.4, 120.8, 122.6, 131.2, 132.4, 133.9, 155.9.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified
  3. customThe product was then recrystallized from ethanol

Sources & evidence

ORD record
ord-68b243a8331445c1992b686fb0c41c7e
Source dataset
uspto-grants-2012_01
Patent number
US08092712B2

Reaction notes

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