Dimethylamine, hydrochloride → HCID 86687936, compound

HRID 2401486Notes

Reaction equation

[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11](O)=[O:12])[O:10][C:6]=2[CH:5]=[C:4]([N+:14]([O-:16])=[O:15])[C:3]=1[O:17][CH3:18].Cl.[CH3:20][NH:21][CH3:22]>>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([N:21]([CH3:22])[CH3:20])=[O:12])[O:10][C:6]=2[CH:5]=[C:4]([N+:14]([O-:16])=[O:15])[C:3]=1[O:17][CH3:18]

Participants

Reactant 2

HCID 10473Dimethylamine, hydrochloride

HCID 71743897HCID 71743897, compound

Product 1

HCID 86687936HCID 86687936, compoundYield 66%

Procedure

4-Chloro-5-methoxy-N,N-dimethyl-6-nitrobenzofuran-2-carboxamide was prepared by the procedure described in Example 1, step 2 starting from 4-chloro-5-methoxy-6-nitrobenzofuran-2-carboxylic acid (1.17 g, 4.31 mmol) an dimethylamine hydrochloride (386 mg, 4.74 mmol). Purification via silica gel column chromatography (20-100% ethyl acetate/isohexane) gave 4-chloro-5-methoxy-N,N-dimethyl-6-nitrobenzofuran-2-carboxamide as a orange solid (850 mg, 66%).

Workup

custom4-Chloro-5-methoxy-N,N-dimethyl-6-nitrobenzofuran-2-carboxamide was prepared by the procedure
customPurification via silica gel column chromatography (20-100% ethyl acetate/isohexane)

Sources & evidence

ORD record: ord-31ce125e4f274bd189df29fe156d83d3
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796296B2

Reaction notes

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