Ethylamine → HCID 68677169, compound

HRID 1992193Notes

Reaction equation

HRID 1992193 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+].[CH2:22]([NH2:24])[CH3:23]>C1C=CC=CC=1>[Cl:1][C:2]1[C:11]([S:12]([NH:24][CH2:22][CH3:23])(=[O:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 11430Potassium CarbonateHCID 20505877HCID 20505877, compound

Product 1

HCID 68677169HCID 68677169, compoundYield 53.4%

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 ethylamine (5.6 mL, 11.2 mmol). Purification of the product provided methyl 2-chloro-3-[(ethylamino)sulfonyl]benzoate (335 mg, 53%) as a solid. 1H NMR (400 MHz, CDCl3), δ 8.24 (dd, 1H, J=8.0, 1.7 Hz), 7.90 (dd, 1H, J=7.8, 1.7 Hz), 7.47 (t, 1H, J=7.8 Hz), 5.14 (t, 1H, J=5.9 Hz), 3.94 (s, 3H), 2.98 (qd, 2H, J=7.3, 6.0 Hz), 1.09 (t, 3H, J=7.2 Hz); ESI-MS 278 (M+H), 300 (M+Na). Methyl 2-chloro-3-[(ethylamino)sulfonyl]benzoate was hydrolyzed using aqueous NaOH to provide 2-chloro-3-[(ethylamino)sulfonyl]benzoic acid as a solid, which was used without further purification. ESI-MS 264 (M+H), 286 (M+Na).

Workup

  1. customPurification of the product

Sources & evidence

ORD record
ord-e53e9dc3ed034c42ba0013a6a97a3f67
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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