2,6-Dichlorobenzoyl chloride → HCID 68193692, compound

HRID 920557Notes

Reaction equation

HRID 920557 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.[Cl:30][C:31]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:32]=1[C:33](Cl)=[O:34]>CC#N>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:33](=[O:34])[C:32]3[C:31]([Cl:30])=[CH:39][CH:38]=[CH:37][C:36]=3[Cl:40])=[CH:18][CH:19]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 783922,6-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 67032498HCID 67032498, compound

Product 1

HCID 68193692HCID 68193692, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-(4-benzyl-morpholin-2-yl)-phenylamine (0.48 g; 1.8 mmol), and N-ethyldiisopropylamine (0.92 mL; 5.4 mmol) in CH3CN (10 mL) was added 2,6-dichlorobenzoyl chloride (0.31 mL; 2.2 mmol), at 0° C. The resulting mixture was allowed to warm to RT, stirred for 1 h, and partitioned between Et2O and 5% aqueous NaHCO3. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O) to afford N-[4-(4-benzyl-morpholin-2-yl)-phenyl]-2,6-dichloro-benzamide (0.61 g).

Workup

  1. customat 0° C
  2. custompartitioned between Et2O and 5% aqueous NaHCO3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (SiO2, Et2O)

Sources & evidence

ORD record
ord-b91d1d22c2e149e99e4af77721243d78
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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