Hydroxyaniline mustard → HCID 9805671, compound

HRID 1699490Notes

Reaction equation

[CH2:1]([C:4]1[C:9](=[O:10])[C:8]([CH3:11])=[C:7]([C:12]([CH3:18])([CH3:17])[CH2:13][C:14]([OH:16])=[O:15])[C:6](=[O:19])[C:5]=1[CH3:20])[CH:2]=[CH2:3].[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>>[CH2:1]([C:4]1[C:9](=[O:10])[C:8]([CH3:11])=[C:7]([C:12]([CH3:18])([CH3:17])[CH2:13][C:14]([O:16][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:15])[C:6](=[O:19])[C:5]=1[CH3:20])[CH:2]=[CH2:3]

Participants

Reactant 2

HCID 71000Hydroxyaniline mustard

HCID 57075710HCID 57075710, compound

Product 1

HCID 9805671HCID 9805671, compoundYield 26%

Procedure

Using an analogous procedure to that described in Example 5, 3-(3-allyl-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-(3-allyl-2,5-dimethyl-1,4-benzoquinonyl)-3-methylbutyrate as an oil in 26% yield; NMR Spectrum: (CDCl3) 1.52 (s, 6H), 1.96 (s, 3H), 2.17 (s, 3H), 3.15 (d, 2H), 3.2 (s, 2H), 3.56-3.72 (m, 8H), 4.99 (m, 2H), 5.72 (m, 1H), 6.58-6.88 (m, 4H); Mass Spectrum: (M+H+) 496,494,492.

Sources & evidence

ORD record: ord-737c5d09c4884af4990a7c993ced5248
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06346633B1

Reaction notes

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