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

HRID 1992191

Reaction equation

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]

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-9a67d6355e9c4e71bceeabf93228a865
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645771B2

Linked notes

Loading…