Butyryl chloride → HCID 178454517, compound

HRID 1056482Notes

Reaction equation

HRID 1056482 reaction equation
[Cl-].[CH3:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]=[N:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH3+:21])=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)=[O:5].[C:22](Cl)(=[O:26])[CH2:23][CH2:24][CH3:25]>N1C=CC=CC=1>[C:22]([NH:21][CH2:20][C:17]1[CH:16]=[CH:15][C:14](/[N:13]=[N:12]/[C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:11][CH:10]=2)=[CH:19][CH:18]=1)(=[O:26])[CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 86695989(4-((4-(Methoxycarbonyl)phenyl)diazenyl)phenyl)methanaminium chloride

Product 1

HCID 178454517HCID 178454517, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into the solution of the amine 4 (915 mg, 3.0 mmol) in pyridine (15 mL) was added dropwise butyryl chloride (477 mg, 4.5 mmol), and the reaction was stirred overnight at room temperature. The solvent was evaporated, the residue dissolved in chloroform, washed with hydrochloric acid (1.0 M), water and brine, and dried with magnesium sulfate. Silica gel chromatography with chloroform as eluent gave pure 10 (916 mg, 90%) as orange crystals. 1H NMR (360 MHz, CDCl3): δ 8.19 (d, J=8.4 Hz, 2H), 7.96-7.91 (m, 4H), 7.44 (d, J=8.0 Hz, 2H), 5.86 (br s, 1H), 4.55 (d, J=6.0 Hz), 3.97 (s, 3H), 2.56 (t, J=7.6 Hz, 2H), 1.73 (q, J=7.6 Hz, 2H), 0.99 (t, J=7.6 Hz, 3H). 13C NMR (100.61 MHz, CDCl3): δ 172.55, 166.14, 154.70, 151.49, 141.99, 131.44, 130.22, 128.06, 123.11, 122.26, 51.95, 42.77, 38.29, 18.78, 13.42. HRMS (m/z): [M+H]+ calcd. for C19H21N3O3 340.1656. found 340.1669.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in chloroform
  3. washwashed with hydrochloric acid (1.0 M), water and brine
  4. dry with materialdried with magnesium sulfate

Sources & evidence

ORD record
ord-14b56b83b80943cda022483d193e7640
Source dataset
uspto-grants-2016_07
Patent number
US09399145B2

Reaction notes

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