Diisopropylethylamine → Tert-butyl 2-((2-chloro-4-sulfamoylphenylamino)methyl)morpholine-4-carboxylate

HRID 574921Notes

Reaction equation

HRID 574921 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[NH2:13][CH2:14][CH:15]1[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]1.C(N(C(C)C)C(C)C)C>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([S:9](=[O:11])(=[O:10])[NH2:12])[CH:5]=[CH:6][C:7]=1[NH:13][CH2:14][CH:15]1[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 75098833-Chloro-4-fluorobenzenesulfonamideHCID 19081094tert-Butyl 2-(aminomethyl)morpholine-4-carboxylate

Product 1

HCID 67126756Tert-butyl 2-((2-chloro-4-sulfamoylphenylamino)methyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3-chloro-4-fluorobenzenesulfonamide (1.0 g), tert-butyl 2-(aminomethyl)morpholine-4-carboxylate (1.135 g) and N-ethyl-N-isopropylpropan-2-amine (1.246 mL) in dimethylsulfoxide (15 mL) was stirred at 115° C. for 72 hours. The mixture was concentrated, and the residue was purified on a silica gel column eluting with 60% ethyl acetate to provide the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified on a silica gel column
  3. washeluting with 60% ethyl acetate

Sources & evidence

ORD record
ord-ac16b639d9524354ac2621e84934090b
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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