Cyclopropanecarbonyl chloride → HCID 59454505, compound

HRID 1097500Notes

Reaction equation

HRID 1097500 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:14][C:15]3[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=3)[C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[O:19])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:34]1([C:37](Cl)=[O:38])[CH2:36][CH2:35]1>N1C=CC=CC=1>[CH:34]1([C:37]([NH:1][C:2]2[S:3][C:4]3[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:14][C:15]4[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=4)[C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=4)=[O:19])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[O:38])[CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 866446963-[(2-amino-7-nitro-1,3-benzothiazol-6-yl)oxy]-N-[3-(trifluoromethyl)phenyl]benzamide

Product 1

HCID 59454505HCID 59454505, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-[(2-amino-7-nitro-1,3-benzothiazol-6-yl)oxy]-N-[3-(trifluoromethyl)phenyl]benzamide (200 mg, 0.421 mmol) in pyridine (4 mL) was added cyclopropanecarbonyl chloride (76 μL, 0.842 mmol), and the mixture was stirred at room temperature for 8 hr. The reaction mixture was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (50 ml), washed successively with 5% aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (50 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=40/60→100/0), and the obtained solution was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (97 mg, 42%) as a pale-yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe obtained residue was diluted with ethyl acetate (50 ml)
  3. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationInsoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=40/60→100/0)
  8. concentrationthe obtained solution was concentrated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-8e388893f7d340d1b7eb4650acc1b957
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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