Triethylamine → HCID 10051057, compound

HRID 503670Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]([CH2:21][CH2:22][OH:23])[C:5]1[C:6]([N+:18]([O-:20])=[O:19])=[CH:7][C:8]([N+:15]([O-:17])=[O:16])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11].CCN(CC)CC.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH3:31][S:32]([O:1][CH2:2][CH2:3][N:4]([CH2:21][CH2:22][O:23][S:32]([CH3:31])(=[O:34])=[O:33])[C:5]1[C:6]([N+:18]([O-:20])=[O:19])=[CH:7][C:8]([N+:15]([O-:17])=[O:16])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])(=[O:34])=[O:33]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of methyl 5-[bis(2-hydroxyethyl)amino]-2,4-dinitrobenzoate [Palmer et al., J. Med. Chem 1994, 37, 2175] (5.50 g, 16.7 mmol) and Et3N (5.82 mL, 41.8 mmol) in dry CH2Cl2 (50 mL) was treated dropwise at 0° C. with MsCl (3.14 mL, 40.0 mmol). After 30 min, 10% aqueous KHCO3 (100 mL) was added, and the mixture was stirred for a further 30 min at 0° C. and then diluted with pet. ether (500 mL). The precipitated product was collected and washed with water and iPr2O to give methyl 5-(bis{2-[(methylsulfonyl)oxy]ethyl}amino)-2,4-dinitrobenzoate (7) (7.44 g, 92%):

Workup

customThe precipitated product was collected
washwashed with water and iPr2O

Sources & evidence

ORD record: ord-6ff8d2f8ef0245338cb89ebc3cd23578
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776924B2

Reaction notes

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