Sodium Hydroxide → 2,5-Dichloro-3-[(methylsulfonyl)amino]benzoic acid hydrochloride
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
Reactant 5
Product 1
Reagents, catalysts & solvents 2
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
- Patent number
- US07645771B2
Reaction notes
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