Triethylamine → HCID 51349701, compound

HRID 1916975Notes

Reaction equation

HRID 1916975 reaction equation
Cl[C:2]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[O:3]1.C(N(CC)CC)C.[NH2:26][CH2:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=1>>[CH:7]1[CH:6]=[C:5]2[C:4]([N:33]([CH2:32][C:31]3[CH:34]=[CH:35][C:28]([C:27]#[N:26])=[CH:29][CH:30]=3)[C:2]([OH:3])([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:10]2=[CH:9][CH:8]=1)=[O:11]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 826084-(Aminomethyl)benzonitrileHCID 126920383-Chloro-3-(4-chlorophenyl)-2-benzofuran-1(3H)-one

Product 1

HCID 51349701HCID 51349701, compoundYield 50%

Procedure

Distilled THF (25 mL) was added to 3-chloro-3-(4-chlorophenyl)-3H-isobenzofuran-1-one (1.071 g, 3.84 mmol) followed by triethylamine (777.14 mg, 7.68 mmol, 1.07 mL) and 4-(aminomethyl)benzonitrile (507.6 mg, 3.84 mmol). The mixture was stirred at room temperature under nitrogen for 4 hours and monitored by TLC. Upon completion the mixture was then extracted with EtOAc (15 mL) and washed with saturated sodium bicarbonate (3×10 mL), water (3×10 mL) and dried (Na2SO4). Removal of solvent after washing produced a viscous orange oil. Trituration under petrol yielded a yellow/orange solid which was recrystallised from a minimum amount of boiling ethyl acetate and excess petrol to produce the title product as a fine pale yellow crystalline solid (665 mg, 1.83 mmol, 50%). 1H NMR: (300 MHz, DMSO) δ ppm 4.31 (d, 2H, J=16.12 Hz, H9), 4.55 (d, 2H J=16.15 Hz, H9′), 7.26 (m, 5H, H1-H5), 7.37 (d, 2H J=8.29 Hz, H10, H13), 7.58 (m, 2H, H6-H7), 7.64 (d, 2H J=8.26 Hz, H11-H12), 7.77 (d, 1H, H8). 13C NMR: (75 Hz, DMSO); δ 42.51 (N—CH2), 60.02 (CN) 90.57 (O—C—N), 109.82, 119.08, 123.06, 123.25, 128.40, 128.62, 129.16, 129.83, 130.54, 132.03, 133.19, 133.26, 133.52, 139.19, 144.24, 149.48 (Ar), 167.23 (C═O). IR: 1397, 1655, 2227 cm−1.

Workup

  1. distillationDistilled THF (25 mL)
  2. extractionUpon completion the mixture was then extracted with EtOAc (15 mL)
  3. washwashed with saturated sodium bicarbonate (3×10 mL), water (3×10 mL)
  4. dry with materialdried (Na2SO4)
  5. customRemoval of solvent
  6. washafter washing
  7. customproduced a viscous orange oil
  8. customTrituration under petrol yielded a yellow/orange solid which
  9. customwas recrystallised from a minimum amount of boiling ethyl acetate and excess petrol

Sources & evidence

ORD record
ord-8d5a1f3aeaea499a82efb5194130085b
Source dataset
uspto-grants-2013_12
Patent number
US08618158B2

Reaction notes

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