4-Chlorobenzaldehyde → HCID 70164883, compound

HRID 1250231Notes

Reaction equation

HRID 1250231 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[N:9]([CH2:14][CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:19][CH2:18]1)[C:8]2=[O:32].[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1>C(O)(=O)C>[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=[CH:13][C:10]2[N:9]([CH2:14][CH2:15][CH2:16][CH:17]3[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][CH2:25][N:26]4[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]4)[CH2:21][CH2:22]3)[C:8](=[O:32])[C:7]3[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=3)[N:11]=2)=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 18327332HCID 18327332, compound

Product 1

HCID 70164883HCID 70164883, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product from Step C (144 mg, 0.33 mmol) and 4-chlorobenzaldehyde (46 mg, 0.33 mmol) in acetic acid (15 mL) was heated at 120° C. for 17 h. The reaction mixture was concentrated under vacuum and the residue was diluted with CHCl3. The organic solution was washed with sat'd aq NaHCO3, sat'd aq NaCl, dried and concentrated. Purification via SiO2-gel chromatography using EtOAc/NEt3 (10:1) yielded the desired product. API-MS: 563 (M+1). 1H NMR (300 MHz, CDCl3): d 8.0 (d, 2 H), 7.8 (d, 1 H), 7.5 (d, 2 H), 7.38 (m, 3 H), 7.15 (d, 1 H), 7.0 (d, 2 H), 4.1 (t, 2 H), 4.0 (s, 3 H), 2.85 (m), 2.3 (m), 1.9-1.2 (m).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionthe residue was diluted with CHCl3
  3. washThe organic solution was washed with sat'd aq NaHCO3
  4. customdried
  5. concentrationconcentrated
  6. customPurification via SiO2-gel chromatography

Sources & evidence

ORD record
ord-05c58666ceb24052a08b17ddcf78dd7f
Source dataset
uspto-grants-2002_01
Patent number
US06337332B1

Reaction notes

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