Water → HCID 9899728, compound

HRID 349668Notes

Reaction equation

HRID 349668 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[CH3:12][C@H:13]1[O:18][C@@H:17]([CH3:19])[CH2:16][NH:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:19][C@H:17]1[O:18][C@@H:13]([CH3:12])[CH2:14][N:15]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=2)[CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 6415002,6-Dimethylmorpholine, cis-

Product 1

HCID 9899728HCID 9899728, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-chloro-2-nitrophenylamine (1.3 g, 7.0 mmol), cis-2,6-dimethylmorpholine (2.5 g, 20 mmol), and K2CO3 (3.0 g, 22 mmol) in DMF (20 mL) was stirred at 110° C. for 48 h. The reaction mixture was cooled to room temperature, poured into water (300 mL). The resulting crude yellow solid was collected by vacuum filtration, air dried, and purified by flash chromatography (silica gel, 4×7.5 cm, eluted with 95/5 CHCl3/ether) to yield the product as a yellow solid (1.2 g, 68%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting crude yellow solid was collected by vacuum filtration, air
  3. customdried
  4. custompurified by flash chromatography (silica gel, 4×7.5 cm, eluted with 95/5 CHCl3/ether)

Sources & evidence

ORD record
ord-afbc72bc8c914f7c872a8f0edff479f0
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Reaction notes

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