Triethylamine → HCID 51349563, compound

HRID 2199281Notes

Reaction equation

HRID 2199281 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.[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1>>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:2]2([OH:3])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[N:32]2[CH2:31][C:30]2[CH:33]=[CH:34][C:27]([Cl:26])=[CH:28][CH:29]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 660364-ChlorobenzylamineHCID 126920383-Chloro-3-(4-chlorophenyl)-2-benzofuran-1(3H)-one

Product 1

HCID 51349563HCID 51349563, compoundYield 83.3%

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 (855.1.1 mg, 8.45 mmol, 1.178 mL) and para-chlorobenzylamine (543.36 mg, 3.84 mmol, 0.467 mL) resulting in the formation of a white precipitate. 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). The solvent was removed under reduced pressure and the resultant precipitate recrystallised (EtOAc, petrol) to give the title product as a fine white crystalline solid (1.191 g, 3.20 mmol, 83%). 1H NMR: (300 MHz, DMSO) δ ppm 4.23 (d, 1H, J=15.59, H9) 4.45 (d, 1H, J=15.62H9′) 7.25 (m, 9H, H1-H5, H10-H13) 7.56 (m, 2H, H6-H7) 7.76 (d, 1H, H8). 13C NMR: (75 Hz, DMSO); δ 42.09 (N—CH2), 90.55 (O—C—N), 122.98, 123.19, 128.02, 128.39, 128.57, 129.76, 130.21, 130.66, 131.60, 133.07, 133.15, 137.44, 139.33, 149.52 (Ar), 167.16 (C═O). Mp: 156.2-156.9° C. IR: 1467, 1661, 3184 cm−1.

Workup

  1. distillationDistilled THF (25 mL)
  2. customresulting in the formation of a white precipitate
  3. extractionUpon completion the mixture was then extracted with EtOAc (15 mL)
  4. washwashed with saturated sodium bicarbonate (3×10 mL), water (3×10 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed under reduced pressure
  7. customthe resultant precipitate recrystallised (EtOAc, petrol)

Sources & evidence

ORD record
ord-522164d9aea84f6093a92ef7b0d47ab0
Source dataset
uspto-grants-2016_06
Patent number
US09358222B2

Reaction notes

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