Hydrochloric Acid → HCID 57855931, compound

HRID 2039615Notes

Reaction equation

[Cl:1][C:2]1[C:3]([F:15])=[C:4]([CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]=1F)[C:5]([OH:7])=[O:6].[CH2:16]([N:18](CC)CC)C.CN.Cl>O.CN>[Cl:1][C:2]1[C:3]([F:15])=[C:4]([CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]=1[NH:18][CH3:16])[C:5]([OH:7])=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 5 g (21.05 mmol) of 3-chloro-2,4-difluoro-5-nitro-benzoic acid (known from WO 03/077914) in 50 mL of H2O is cooled to a temperature of 0° C. Then 5.86 ml (42.10 mmol) of triethylamine were added dropwise followed by the dropwise addition of 1.82 ml (21.05 mmol) of methylamine (40% in H2O). After 30 min of stirring at 0° C., 0.18 ml (2.11 mmol) of methylamine (40% in H2O) is added and the mixture is stirred again during 30 min at a temperature of 0° C. The pH of the mixture is adjusted to 1-0.5 by the addition of concentrated HCl at a temperature of 0° C. The product is extracted with tert-butyl methyl ether (2 times) and the organic phase is washed once with brine, dried on Na2SO4, filtrated and the solvent is evaporated. 5.35 g (21.52 mmol, 102%) of a crude yellow solid were obtained and used directly in the next step without purification. LC/MS: 247/249 (M−1)−.

Workup

stirringthe mixture is stirred again during 30 min at a temperature of 0° C
extractionThe product is extracted with tert-butyl methyl ether (2 times)
washthe organic phase is washed once with brine
customdried on Na2SO4
filtrationfiltrated
customthe solvent is evaporated

Sources & evidence

ORD record: ord-c6e2d1c1f97d4b8bb389489de4a9808b
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580785B2

Reaction notes

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