Hydroxyaniline mustard → HCID 9956815, compound

HRID 1699494Notes

Reaction equation

[CH3:1][CH:2]([C:6]([CH3:19])([C:8]1[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[C:10](=[O:17])[C:9]=1[CH3:18])[CH3:7])[C:3]([OH:5])=[O:4].[Cl:20][CH2:21][CH2:22][N:23]([CH2:31][CH2:32][Cl:33])[C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1>>[CH3:1][CH:2]([C:6]([CH3:19])([C:8]1[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[C:10](=[O:17])[C:9]=1[CH3:18])[CH3:7])[C:3]([O:5][C:27]1[CH:26]=[CH:25][C:24]([N:23]([CH2:22][CH2:21][Cl:20])[CH2:31][CH2:32][Cl:33])=[CH:29][CH:28]=1)=[O:4]

Participants

Reactant 2

HCID 71000Hydroxyaniline mustard

HCID 69963716HCID 69963716, compound

Product 1

HCID 9956815HCID 9956815, compoundYield 20%

Procedure

Using an analogous procedure to that described in Example 1, 2,3-dimethyl-3-(2,3,5-trimethyl-1,4-benzoquinonyl)butyric acid was reacted with 4-[bis(2-chloroethyl)amino]phenol and the product was purified by column chromatography on silica using a 8.5:1.5 mixture of petroleum ether (b.p. 40 to 60° C.) and ethyl acetate as eluent. There was thus obtained to give 4-[bis(2-chloroethyl)amino]phenyl 2,3-dimethyl-3-(2,3,5-trimethyl-1,4-benzoquinonyl)butyrate as an oil in 20% yield; NMR Spectrum: (CDCl3) 1.25 (d, 3H), 1.45 (s, 3H), 1.50 (s, 3H), 1.95 (s, 3H), 1.97 (s, 3H), 2.21 (s, 3H), 3.60 (t, 4H), 3.67 (t, 4H), 3.85 (q, 1H), 6.61 (d, 2H), 6.82 (d, 2H); Mass Spectrum: (M+Na+) 502, 504 & 506.

Workup

customthe product was purified by column chromatography on silica using
additiona 8.5:1.5 mixture of petroleum ether (b.p. 40 to 60° C.) and ethyl acetate as eluent
customThere was thus obtained

Sources & evidence

ORD record: ord-0619973fd8b146b2805128afde783cb0
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06346633B1

Reaction notes

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