Dichloromethane → HCID 91515042, compound

HRID 1932448Notes

Reaction equation

HRID 1932448 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=2)=[C:9]([O:23][CH3:24])[CH:8]=1)[CH3:2].ClCCl.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C1COCC1.CN(C)C1C=CN=CC=1.O.CN(C=O)C>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][N:6]([S:37]([CH3:36])(=[O:39])=[O:38])[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=2)=[C:9]([O:23][CH3:24])[CH:8]=1)[CH3:2]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131729742HCID 131729742, compound

Product 1

HCID 91515042HCID 91515042, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

A solution of ethyl[3-methoxy-4-(5-nitropyridin-2-yloxy)phenylamino]acetate (2.43 g, 7.00 mmol) was dissolved in THF (15 mL), dichloromethane (20 mL) and DMF (10 mL), and to the resulting solution were added triethylamine (1.95 mL, 13.99 mmol), 4-dimethylaminopyridine (0.86 g, 7.00 mmol) and methanesulfonyl chloride (1.08 mL, 13.99 mmol) under ice cooling. The resulting solution was stirred for 14 hours at 30° C. Water was added to the reaction mixture, and extracted with dichloromethane. The dichloromethane layer was washed with water and brine. The dichloromethane layer was dried over anhydrous magnesium sulfate, evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2), to thereby yield 1.10 g of the title compound.

Workup

  1. extractionextracted with dichloromethane
  2. washThe dichloromethane layer was washed with water and brine
  3. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-86c9cf215a2e492fa131c41a8a62abfd
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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