1-Butanol → 1204408-18-3

HRID 1842581Notes

Reaction equation

HRID 1842581 reaction equation
Cl[C:2]1[C:3]2[CH:11]=[C:10]([CH3:12])[O:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[CH3:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:21]([OH:25])CCC.CO>Cl.CCCCCC>[CH3:21][O:25][C:18]1[CH:19]=[CH:20][C:15]([N:14]([CH3:13])[C:2]2[C:3]3[CH:11]=[C:10]([CH3:12])[O:9][C:4]=3[N:5]=[C:6]([CH3:8])[N:7]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 2631-ButanolHCID 887MethanolHCID 7515N-MethylanilineHCID 57428968HCID 57428968, compound2×

Product 1

HCID 446119191204408-18-3

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8058HexaneSolvent

Procedure

To a 50 mL flask was added 5 (91 mg, 0.5 mmol), 6 (77 mg, 0.55 mmol) and 5 mL BuOH. To this solution was added 2 drops of concentrate HCl solution and the mixture was refluxed. TLC indicated the disappearance of starting material 5, the solvent was removed under reduced pressure. To the residue obtained was added silica gel and MeOH and the solvent removed to make a plug. This plug was separated by column chromatography to give 106 g (75%) of AGG1 as a white powder: TLC Rf0.36 (Hexane/EtOAC 3:1); mp 108-109° C.; 1H NMR (DMSO-d6) δ 2.14 (s, 3 H), 2.45 (s, 3 H), 3.43 (s, 3 H), 3.81 (s, 3 H), 4.55 (s, 1 H), 7.04 (d, 2 H, J=2.8 Hz), 7.25 (d, 2 H, J=28 Hz). Anal. (C16H17N3O2) m/z (ESI) 284.1387 [M+1]+.

Workup

  1. temperaturethe mixture was refluxed
  2. customthe solvent was removed under reduced pressure
  3. customTo the residue obtained
  4. customthe solvent removed
  5. customThis plug was separated by column chromatography
  6. customto give 106 g (75%) of AGG1 as a white powder

Sources & evidence

ORD record
ord-eab9c827d97f4aa98a06058fad369586
Source dataset
uspto-grants-2015_02
Patent number
US08946239B2

Reaction notes

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