Pyridine → Ethyl 4-methoxy-3-(methylsulfonamido)phenyl carbonate

HRID 1776588Notes

Reaction equation

HRID 1776588 reaction equation
[C:1](=[O:15])([O:12][CH2:13][CH3:14])[O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([NH2:11])[CH:4]=1.N1C=CC=CC=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[C:1](=[O:15])([O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([NH:11][S:23]([CH3:22])(=[O:25])=[O:24])[CH:4]=1)[O:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 134556543-Amino-4-methoxyphenyl ethyl carbonate

Product 1

HCID 86679540Ethyl 4-methoxy-3-(methylsulfonamido)phenyl carbonateYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-4-methoxyphenyl ethyl carbonate (0.650 g, 3.08 mmol) and pyridine (2.2 ml, 27.2 mmol) in dry DCM (20 ml), methanesulfonyl chloride (1.0 ml, 12.83 mmol) was added at RT, and the resulting mixture was stirred for 3 hours. The volatiles were removed under reduced pressure affording crude ethyl 4-methoxy-3-(methylsulfonamido)phenyl carbonate (0.850 g, 2.94 mmol, 95% yield, MS/ESI+312.1 [MNa]+) which was used for the next step without purification.

Workup

  1. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-bab5a4184e9d4eafbb68d22917e4a23f
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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