N-[(4-tert-butylphenyl)methylidene]hydroxylamine → methyl 4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[(4-phenylbenzoyl)amino]benzoate

HRID 29695Notes

Reaction equation

HRID 29695 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13]Br)=[CH:6][C:5]=1[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)=[O:17].[C:31]([C:35]1[CH:43]=[CH:42][C:38]([CH:39]=[N:40][OH:41])=[CH:37][CH:36]=1)([CH3:34])([CH3:33])[CH3:32]>CC(C)=O>[C:21]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:22]=[CH:23][C:18]([C:16]([NH:15][C:5]2[CH:6]=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:41]/[N:40]=[CH:39]/[C:38]3[CH:37]=[CH:36][C:35]([C:31]([CH3:34])([CH3:32])[CH3:33])=[CH:43][CH:42]=3)[CH:8]=[CH:9][C:4]=2[C:3]([OH:30])=[O:2])=[O:17])=[CH:19][CH:20]=1.[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:41]/[N:40]=[CH:39]/[C:38]2[CH:42]=[CH:43][C:35]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:36][CH:37]=2)=[CH:6][C:5]=1[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)=[O:17]

Participants

5

Reactant 2

HCID 1275951N-[(4-tert-butylphenyl)methylidene]hydroxylamineHCID 574195312-[(Biphenyl-4-carbonyl)-amino]-4-(3-bromo-propoxy)-benzoic acid methyl ester

Product 2

HCID 117861574-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[(4-phenylbenzoyl)amino]benzoic acidHCID 87734645methyl 4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[(4-phenylbenzoyl)amino]benzoateYield 131.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The desired product was prepared using a procedure similar to Step 6 of example 34. Thus, 2-[(biphenyl-4-carbonyl)-amino]-4-(3-bromo-propoxy)-benzoic acid methyl ester (0.325 g, 0.694 mmol) was reacted with Cs2Co3 (0.475 g, 1.457 mmol) and 4-tert-Butyl-benzaldehyde oxime (0.135 g, 0.763 mmol) in acetone (30 ml) to give 2-[(1,1′-biphenyl-4-ylcarbonyl)amino]-4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid methyl ester (0.258 g, 0.457 mmol, 66%) as a viscous yellow oil. 1H NMR (DMSO-d6) δ 1.20 (s, 9H), 2.05-2.18 (m, 2H), 3.85 (s, 3H), 4.18 (t, 2H), 4.23 (t, 2H), 6.79 (d, 1H), 7.32-7.50 (m, 7H), 7.73 (d, 2H), 7.85 (d, 2H), 7.95-8.02 (m, 3H), 8.18 (s, 1H), 8.39 (s, 1H), 11.98 (s, 1H), mass spectrum [ES(+)], m/z 565 (M+H)+.

Sources & evidence

ORD record
ord-f69b2f90cf3649c69d08c8af645f9ede
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

Loading…