Methylamine → HCID 68677270, compound

HRID 1992211Notes

Reaction equation

HRID 1992211 reaction equation
[Cl:1][C:2]1[C:11]([S:12](Cl)(=[O:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH3:22][NH2:23].C1COCC1>C1C=CC=CC=1>[Cl:1][C:2]1[C:11]([S:12]([NH:23][CH3:22])(=[O:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 20505877HCID 20505877, compound

Product 1

HCID 68677270HCID 68677270, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of methyl 2-chloro-3-(chlorosulfonyl)benzoate (608 mg, 2.26 mmol) and K2CO3 (770 mg, 5.6 mmol) in 10 mL benzene was added a 2M solution of methylamine in THF (5.6 mL, 11.2 mmol). Purification of the product (2:1 hex:EtOAc) provided methyl 2-chloro-3-[(methylamino)sulfonyl]benzoate (430 mg, 72%) as a solid. 1H NMR (400 MHz, CDCl3), δ 8.23 (dd, 1H, J=7.9, 1.7 Hz), 7.90 (dd, 1H, J=7.8, 1.7 Hz), 7.48 (t, 1H, J=7.9 Hz), 5.16 (q, 1H, J=5.2 Hz), 3.94 (s, 3H), 2.62 (d, 3H, J=5.3 Hz); ESI-MS 264 (M+H). Methyl 2-chloro-3-[(methylamino)sulfonyl]benzoate was hydrolyzed using aqueous NaOH to provide 2-chloro-3-[(methylamino)sulfonyl]benzoic acid as a solid, which was used without further purification. ESI-MS 250 (M+H), 272 (M+Na).

Workup

  1. customPurification of the product (2:1 hex:EtOAc)

Sources & evidence

ORD record
ord-aa72eee1a3d74a7c97f8d378f57f4a43
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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