Hydrochloric Acid → HCID 67005686, compound

HRID 564289Notes

Reaction equation

HRID 564289 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.[C:17]([NH:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>O1CCCC1.C(OCC)(=O)C>[S:8]1[C:4]2[CH:3]=[C:2]([NH:1][C:29](=[O:30])[C:28]3[CH:32]=[CH:33][CH:34]=[C:26]([NH:25][C:17](=[O:24])[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:27]=3)[CH:10]=[CH:9][C:5]=2[N:6]=[CH:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 682886-AminobenzothiazoleHCID 184700593-Benzamidobenzoyl chloride

Product 1

HCID 67005686HCID 67005686, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.1 g of 6-aminobenzothiazole and 0.1 g of pyridine added to 5 ml of tetrahydrofuran and stirred at room temperature was introduced dropwise 0.2 g of 3-(benzoylamino)benzoyl chloride dissolved in 1 ml of tetrahydrofuran. The resulting solution was stirred at room temperature for 1 hour, and then ethyl acetate and 1N hydrochloric acid were added thereto for separating the organic phase. The organic phase was washed with saturated sodium hydrogen carbonate solution one time, and then dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain 0.15 g of the desired product (Yield: 52%) as a white solid.

Workup

  1. stirringThe resulting solution was stirred at room temperature for 1 hour
  2. customfor separating the organic phase
  3. washThe organic phase was washed with saturated sodium hydrogen carbonate solution one time
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution was filtered off
  6. customthe filtrate was collected
  7. customthe solvent was removed under a reduced pressure
  8. customto obtain a residue
  9. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-7d742ced661e432cbf55e82b4c071c9f
Source dataset
uspto-grants-2011_11
Patent number
US08067638B2

Reaction notes

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