Chloroform → HCID 59813240, compound

HRID 1925296Notes

Reaction equation

HRID 1925296 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][CH3:22])=[O:20])[CH:14]=1)=[CH:7]2.C([O-])(O)=O.[Na+].[Cl:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32](Cl)=[O:33].C(Cl)(Cl)Cl>C(Cl)Cl>[CH3:22][NH:21][C:19]([C:15]1[CH:14]=[C:13]([O:12][C:6]2[CH:5]=[CH:4][C:3]3[C:8](=[CH:9][CH:10]=[CH:11][C:2]=3[NH:1][C:32]([C:31]3[CH:35]=[CH:36][CH:37]=[C:29]([Cl:28])[CH:30]=3)=[O:33])[CH:7]=2)[CH:18]=[CH:17][N:16]=1)=[O:20]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 69252Benzoyl chloride, 3-chloro-HCID 516892Sodium BicarbonateHCID 67519936HCID 67519936, compound

Product 1

HCID 59813240HCID 59813240, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(5-aminonaphthalen-2-yloxy)-N-methylpicolinamide (40 mg, 0.14 mmol) and NaHCO3 (33 mg, 0.44 mmol)in CH2Cl2, 3-chlorobenzoyl chloride (17 □L, 0.14 mmol) was added. The reaction was stirred at RT for 12 h then taken up into CHCl3 and washed with water and brine, dried over Na2SO4, and filtered. The title compound was isolated after purification by column chromatography. MS (ESI pos. ion) m/z: 432.4 (M+H). Calc'd for C24H18ClN3O3−431.87.

Workup

  1. additionwas added
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-caf9cc9283d64d7e8baf0c45530e1004
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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