Triethylamine → HCID 51349563, compound

HRID 2381574Notes

Reaction equation

HRID 2381574 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.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1.C(N(CC)CC)C>>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:25]2[C:2]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)([OH:3])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])=[CH:22][CH:21]=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 43%

Procedure

Distilled THF (50 mL) was added to 3-chloro-3-(4-chlorophenyl)isobenzofuran-1(3H)-one (1.50 g, 5.76 mmol) followed by 4-chlorobenzylamine (0.77 mL, 6.34 mmol) and triethylamine (0.96 mL, 6.91 mmol) as for general procedure A and recrystallised in acetonitrile to give pure white solid 2-(4-chlorobenzyl)-3-(4-chlorophenyl)-3-hydroxyisoindolin-1-one (945 mg, 2.46 mmol. 43%). Rf 0.54 (40:60 EtOAc:petrol). Mp. 156.5-157.4° C. λmax (CH3OH)/nm 221.0, Abs 0.850. IR: 3159, 1659, 1487, 1468 cm−1. 1H NMR (300 Hz, CDCl3); δ 3.07 (s, br, 1H, OH), 4.01 (d, 1H, J=15.0 Hz, N—CH2), 4.52 (d, 1H, J=15.0 Hz, N—CH2), 7.05 (m, 4H, Ar—H), 7.16-7.21 (m, 5H, Ar—H), 7.42 (m, 2H, Ar—H), 7.73 (m, 1H, Ar—H). 13C NMR (75 Hz, DMSO); δ 42.6 (N—CH2), 91.5 (Ar2(O)CN), 123.1, 124.0, 128.2, 128.7, 129.1, 130.4, 130.6, 133.4, 133.5, 135.0, 136.8, 137.0, 148.8 (Ar), 168.0 (C═O). LC/MS-ES+ m/z 406.1, 366.0, 244.9, 242.9, 161.0. Anal. Calcd. for C21H15Cl2NO2.0.2H2O: C, 65.03; H, 4.00; N, 3.61%. Found C, 65.08; H, 4.06; N, 3.88%. HRMS (EI) m/z: 244.0291. Found 244.0299.

Workup

  1. distillationDistilled THF (50 mL)
  2. customrecrystallised in acetonitrile

Sources & evidence

ORD record
ord-aaef3b02b3ed40d58c19bbb82707f07f
Source dataset
uspto-grants-2012_09
Patent number
US08258175B2

Reaction notes

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