Hydroxyaniline mustard → HCID 9803896, compound

HRID 1699492Notes

Reaction equation

[CH3:1][C:2]1[C:3](=[O:17])[CH:4]=[C:5]([CH3:16])[C:6](=[O:15])[C:7]=1[C:8]([CH3:14])([CH3:13])[CH2:9][C:10]([OH:12])=[O:11].[Cl:18][CH2:19][CH2:20][N:21]([CH2:29][CH2:30][Cl:31])[C:22]1[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=1>>[CH3:1][C:2]1[C:3](=[O:17])[CH:4]=[C:5]([CH3:16])[C:6](=[O:15])[C:7]=1[C:8]([CH3:13])([CH3:14])[CH2:9][C:10]([O:12][C:25]1[CH:24]=[CH:23][C:22]([N:21]([CH2:20][CH2:19][Cl:18])[CH2:29][CH2:30][Cl:31])=[CH:27][CH:26]=1)=[O:11]

Participants

Reactant 2

HCID 71000Hydroxyaniline mustard

HCID 10561779HCID 10561779, compound

Product 1

HCID 9803896HCID 9803896, compoundYield 9%

Procedure

Using an analogous procedure to that described in Example 5, 3-(2,5-dimethyl-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-1,4-benzoquinonyl)-3-methylbutyrate as a solid in 9% yield; NMR Spectrun: (CDCl3) 1.52 (s, 6H), 1.98 (m, 3H), 2.16 (s, 3H), 3.2 (s, 2H), 3.55-3.73 (m, 8H), 6.42 (m, 1 H), 6.6-6.9 (m, 4H); Mass Spectrum: (M+H+) 452.

Sources & evidence

ORD record: ord-e06f6691981c44d49c270488a2d1be9f
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06346633B1

Reaction notes

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