Sodium Hydroxide → 2,5-Dichloro-3-[(methylsulfonyl)amino]benzoic acid hydrochloride

HRID 1992191

Reaktionsgleichung

NC1C(Cl)=C(C=C([Cl:12])C=1)C(OC)=O.CCN(C(C)C)C(C)C.CS(Cl)(=O)=O.[Cl:28][C:29]1[C:38]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])=[CH:37][C:36]([Cl:44])=[CH:35][C:30]=1[C:31]([O:33]C)=[O:32].[OH-].[Na+]>C(Cl)Cl.CO>[ClH:12].[Cl:28][C:29]1[C:38]([NH:39][S:40]([CH3:43])(=[O:41])=[O:42])=[CH:37][C:36]([Cl:44])=[CH:35][C:30]=1[C:31]([OH:33])=[O:32]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

From common intermediate methyl 3-amino-2,5-dichlorobenzoate following the procedure outlined in scheme. Methyl 3-amino-2,5-dichlorobenzoate (2.10 g, 9.55 mmol), DIEA (3.0 ml) were stirred in DCM (40 ml) at 0° C. methanesulfonyl chloride (2.18 g, 19.08 mmol) was added dropwise whike stirring at 0° C. After 2 hrs at 0° C., reaction was allowed to warm to room temperature while stirring overnight. Quenched rxn with saturated NH4Cl and washed with brine. Organic layer with dried to yield crude methyl 2,5-dichloro-3-[(methylsulfonyl)amino]benzoate (3.10 g) which will be carried on. methyl 2,5-dichloro-3-[(methylsulfonyl)amino]benzoate (3.10 g) was treated with NaOH, methanol following procedure outlined in scheme to form 2,5-dichloro-3-[(methylsulfonyl)amino]benzoic acid hydrochloride (3.53 g).

Aufarbeitung

additionwas added dropwise
customreaction
temperatureto warm to room temperature
stirringwhile stirring overnight
customQuenched
washwashed with brine
customOrganic layer with dried
customto yield crude methyl 2,5-dichloro-3-[(methylsulfonyl)amino]benzoate (3.10 g) which

Quellen und Nachweise

ORD-Eintrag: ord-9a67d6355e9c4e71bceeabf93228a865
Quelldatensatz: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07645771B2

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