Methyl chloroformate → HCID 21280090, compound

HRID 2291372Notes

Reaction equation

[CH2:1]([CH2:8][NH:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[NH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:21]([O:23][CH3:24])=[O:22]>C(COC)OC.N1C=CC=CC=1>[CH2:1]([CH2:8][NH:9][C:10]1[CH:11]=[C:12]([NH:13][C:21](=[O:22])[O:23][CH3:24])[CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A stirred solution of 3-(N-benzylmethylamino)-4-nitroaniline (2.2 g, 8.5 mM) in dry dimethoxyethane (15 ml) and pyridine (4 ml) was treated dropwise with methyl chloroformate (10 mM) at 0° C. The mixture was allowed to warm slowly to 20° C. and after 3 h was quenched with water (5 ml). Volatile solvents were removed under vacuum and the residue was extracted with ethyl acetate. After successive washings with aqueous methanesulfonic acid, water, aqueous KHCO3 and brine the organic layer was dried over Na2SO4. Removal of the solvent and chromatography of the residue on silica gel in ethyl acetate-petroleum ether (3:7) gave the product as a bright red oil (2.25 g, 84% yield).

Workup

customwas quenched with water (5 ml)
customVolatile solvents were removed under vacuum
extractionthe residue was extracted with ethyl acetate
washAfter successive washings with aqueous methanesulfonic acid, water, aqueous KHCO3 and brine the organic layer
dry with materialwas dried over Na2SO4
customRemoval of the solvent and chromatography of the residue on silica gel in ethyl acetate-petroleum ether (3:7)

Sources & evidence

ORD record: ord-2d311e6ea0134a09b9caf43ed7b40102
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04795826

Reaction notes

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