Hydrochloric Acid → N-(3-Chloro-3-methyl-2-nitrosobutyl)-5-nitro-2-furancarboxamide

HRID 1377393Notes

Reaction equation

[CH3:1][C:2]([CH3:16])=[CH:3][CH2:4][NH:5][C:6]([C:8]1[O:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1)=[O:7].[ClH:17].[N:18]([O:20]CCC(C)C)=O>>[Cl:17][C:2]([CH3:16])([CH3:1])[CH:3]([N:18]=[O:20])[CH2:4][NH:5][C:6]([C:8]1[O:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1)=[O:7]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 8053Isoamyl Nitrite

HCID 18929144N-(3-Methyl-2-butenyl)-5-nitro-2-furancarboxamide

Product 1

HCID 18929168N-(3-Chloro-3-methyl-2-nitrosobutyl)-5-nitro-2-furancarboxamide

Conditions

Temperature: -5 °C

Procedure

N-(3-Methyl-2-butenyl)-5-nitro-2-furancarboxamide (2.2 g, 0.01 mol) was suspended in isoamyl nitrite (60 mL) and cooled to -5° C. Concentrated HCl (1 mL, 37%, 0.01 mol) was added through a syringe. The reaction mixture was stirred at -5° C. for 30 min and at room temperature for 30 min. The solid was filtered and washed with chilled (-10° C.) ethanol-ether [100 mL). A light green powder was obtained. Yield: 1.5 g (52%). mp 110°-112° C. MS m 254 [(M+H)-HCl]+. 1H NMR (DMSO-d6) δ1.82 [s, 6H, (C H3)2C=], 4.28 (d, 2H, C H2C=N), 7.49 and 7.75 (d, 2H, furanyl-H), 8.66 (t, 1H, N HCO), 11.72 (s, 1H, C=NO H).

Workup

filtrationThe solid was filtered
washwashed
temperaturewith chilled (-10° C.) ethanol-ether [100 mL)
customA light green powder was obtained

Sources & evidence

ORD record: ord-67d207d0ea9547009b73c73c16a9acfa
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665329

Reaction notes

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