Diethylamine → HCID 86650088, compound

HRID 919201Notes

Reaction equation

HRID 919201 reaction equation
[C:1]([C:5]1[CH:12]=[C:11]([CH2:13][Cl:14])[CH:10]=[C:7]([CH:8]=[O:9])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17]>C(#N)C>[ClH:14].[C:1]([C:5]1[CH:12]=[C:11]([CH2:13][N:18]([CH2:19][CH3:20])[CH2:16][CH3:17])[CH:10]=[C:7]([CH:8]=[O:9])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 158215393-tert-Butyl-5-(chloromethyl)-2-hydroxybenzaldehyde

Product 1

HCID 86650088HCID 86650088, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 3-tert-butyl-5-chloromethylsalicylaldehyde (5)(226.5 mg, 1 mmol) in acetonitrile (60 mL), diethylamine (1 mmol) was added dropwise to give a greenish solution. The reaction was stirred at 30° C. overnight. After evaporation of volatiles, a green oil was obtained which was used without any purification for the next step. Yield: 77%. Green oil. □max 3300, 2899 and 1720 cm−1. 1H-NMR δH: 1.35 (9H, s, C(CH3)3), 1.45 (6H, t, J=7.2 Hz, 2×CH2CH3), 3.43 (4H, q, J=7.2 Hz, 2×CH2CH3), 4.90 (2H, s, CCH2N), 7.57 (1H, d, J=2.1 Hz, HAr), 8.03 (1H, d, J=2.1 Hz, HAr), 9.98 (1H, s, CHO), 12.00 (1H, br s, OH). 13C-NMR δC(CDCl3, 75 MHz): 10.8, 28.3, 33.7, 45.8, 56.0, 119.5, 129.8, 130.3, 133.7, 137.0, 159.0, 195.9.

Workup

  1. customto give a greenish solution
  2. customAfter evaporation of volatiles
  3. customa green oil was obtained which
  4. customwas used without any purification for the next step

Sources & evidence

ORD record
ord-3bc0e10bd1e4407c9e5d83708b12802f
Source dataset
uspto-grants-2016_03
Patent number
US09273024B2

Reaction notes

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