Ethyl Acetate → 4-Benzamido-4'-aminoazobenzene

HRID 881789

Reaction equation

HRID 881789 reaction equation
[N:1]([C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)=[N:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C([O:20][CH2:21][CH3:22])(=O)C>ClCCl>[C:21]([NH:14][C:13]1[CH:15]=[CH:16][C:10]([N:1]=[N:2][C:3]2[CH:4]=[CH:5][C:6]([NH2:7])=[CH:8][CH:9]=2)=[CH:11][CH:12]=1)(=[O:20])[C:22]1[CH:8]=[CH:9][CH:3]=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 108554,4'-Diazenediyldianiline

Product 1

HCID 866570184-Benzamido-4'-aminoazobenzeneYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the general monoacylation procedure, 4,4′-azodianiline (50 mg, 240 μmol) was treated with benzoyl choloride (26 μl, 240 μmol). Silica gel chromatography through a wide column (10% ethyl acetate in dichloromethane) provided S5 as an orange solid (44 mg, 130 μmol, 54% yield): 1H (DMSO, 400 MHz): 6.04 (s, 2H); 6.66 (d, 2H, J=8.4); 7.52-7.65 (m, 5H); 7.76 (d, 2H, J=8.8); 7.88-7.98 (m, 4H); 10.46 (s, 1H). 13C (DMSO, 100 MHz): 113.4, 120.5, 122.3, 124.9, 127.7, 128.4, 131.7, 134.8, 140.4, 142.9, 148.4, 152.5, 165.7. HRMS (ESI+): calc'd for C19H17N4O+—317.1397, found—317.1403 (MH+).

Workup

  1. additionwas treated with benzoyl choloride (26 μl, 240 μmol)

Sources & evidence

ORD record
ord-f2ae17afbcd74cb5b424daa8c36b43af
Source dataset
uspto-grants-2015_03
Patent number
US08993736B2

Linked notes

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