Chlorosuccinimide → HCID 57785872, compound

HRID 1629005Notes

Reaction equation

HRID 1629005 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]2=[N:15][C:16]3[C:17](=[C:18]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH:19]=[CH:20][CH:21]=3)[N:13]2[CH2:12][CH2:11][O:10]1.[Cl:27]N1C(=O)CCC1=O>C(#N)C.C(=O)([O-])O.[Na+].O>[Cl:27][C:21]1[CH:20]=[CH:19][C:18]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[C:17]2[C:16]=1[N:15]=[C:14]1[CH:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[O:10][CH2:11][CH2:12][N:13]21.[Cl:27][C:19]1[C:18]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[C:17]2[N:13]3[CH2:12][CH2:11][O:10][CH:9]([C:3]4[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=4[Cl:1])[C:14]3=[N:15][C:16]2=[CH:21][CH:20]=1

Participants

7

Reactant 2

HCID 31398ChlorosuccinimideHCID 57786068HCID 57786068, compound

Product 2

HCID 57785872HCID 57785872, compoundHCID 57786002HCID 57786002, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-(2,4-dichlorophenyl)-N,N-diethyl-3,4-dihydro-1H-[1,4]oxazino[4,3-a]benzimidazol-6-amine (500 mg, 1.28 mmol) in acetonitrile (13 mL) was added N-chlorosuccinimide (171 mg, 1.28 mmol) at room temperature. After the resultant mixture was stirred at 60° C. for 5 h, the mixture was diluted with aqueous sodium hydrogen carbonate and water, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 25-75% ethyl acetate/n-hexane gradient mixture and preparative HPLC eluting with a 10-100% acetonitrile/water to give 9-chloro-1-(2,4-dichlorophenyl)-N,N-diethyl-3,4-dihydro-1H-[1,4]oxazino[4,3-a]benzimidazol-6-amine as a colorless amorphous solid (Example 502, long retention time on HPLC, 128 mg, 0.302 mmol, 24%), and 7-chloro-1-(2,4-dichlorophenyl)-N,N-diethyl-3,4-dihydro-1H-[1,4]oxazino[4,3-a]benzimidazol-6-amine as a colorless amorphous solid (Example 503, short retention time on HPLC, 160 mg, 0.378 mmol, 30%)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a 25-75% ethyl acetate/n-hexane gradient mixture and preparative HPLC
  7. washeluting with a 10-100% acetonitrile/water

Sources & evidence

ORD record
ord-a3bb37868f4d4956b647af0b51e58b4b
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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