Acetic Anhydride → HCID 18542894, compound

HRID 869058Notes

Reaction equation

HRID 869058 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Cl:8][C:9]1[CH:10]=[C:11]([NH2:16])[CH:12]=[C:13]([NH2:15])[CH:14]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[NH2:16][C:11]1[CH:12]=[C:13]([NH:15][C:5](=[O:7])[CH3:6])[CH:14]=[C:9]([Cl:8])[CH:10]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 733351,3-Benzenediamine, 5-chloro-

Product 1

HCID 18542894HCID 18542894, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

DMAP (50 mg) and acetic anhydride (3.9 g, 37.9 mmol) were added sequentially and dropwise to a cold solution of 5-chloro-benzene-1,3-diamine (4.5 g, 31.6 mmol) in pyridine (22 mL) keeping the internal temperature below 0° C. The reaction mixture was allowed to warm to rt, stirred for 2 h, cooled to 0° C., quenched by addition of ice cooled water, and extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH, 99:1) to afford the title compound. tR: 0.18 min (LC-MS 2); ESI-MS: 184.9 [M+H]+ (LC-MS 2); Rf=0.32 (hexane/EtOAc, 1:4).

Workup

  1. customthe internal temperature below 0° C
  2. temperaturecooled to 0° C.
  3. customquenched by addition of ice
  4. temperaturecooled water
  5. extractionextracted with EtOAc
  6. washThe organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material was purified by silica gel column chromatography (CH2Cl2/MeOH, 99:1)

Sources & evidence

ORD record
ord-c97cc895a31047a3bb4c7499ca828f09
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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