Hydroxyaniline mustard → HCID 57207800, compound

HRID 1699491Notes

Reaction equation

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

Participants

Reactant 2

HCID 71000Hydroxyaniline mustard

HCID 57115966HCID 57115966, compound

Product 1

HCID 57207800HCID 57207800, compoundYield 32%

Procedure

Using an analogous procedure to that described in Example 5, 3-(2,5-dimethyl-3-propyl-1,4-benzoquinonyl)-3-methylbutyric acid was reacted with 4-[bis(2-chloroethyl)amino]phenol to give 4-[bis(2-chloroethyl)amino]phenyl 3-(2,5-dimethyl-3-propyl-1,4-benzoquinonyl)-3-methylbutyrate in 32% yield; NMR Spectrum: (CDCl3) 0.91 (t, 3H), 1.39 (m, 2H), 1.52 (s, 6H), 1.95 (s, 3H), 2.18 (s, 3H), 2.35 (t, 2H), 3.2 (s, 2H), 3.55-3.73 (m, 8H), 6.6 (d, 2H), 6.84 (d, 2H); Mass Spectrum: (M+H+) 498, 496, 494.

Sources & evidence

ORD record: ord-ae7b9c8c32ee47ec8e29238c260b559f
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06346633B1

Reaction notes

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