Benzothiazole → HCID 18518681, compound

HRID 1369119Notes

Reaction equation

HRID 1369119 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Li]CCCC.[CH2:15]([N:17]([CH2:32][CH3:33])[CH2:18][CH2:19][N:20]1[C:30]2[C:25](=[C:26]([Br:31])[CH:27]=[CH:28][CH:29]=2)[C:23](=[O:24])[C:21]1=[O:22])[CH3:16].[NH4+].[Cl-]>C1COCC1>[CH2:32]([N:17]([CH2:15][CH3:16])[CH2:18][CH2:19][N:20]1[C:30]2[C:25](=[C:26]([Br:31])[CH:27]=[CH:28][CH:29]=2)[C:23]([OH:24])([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[C:21]1=[O:22])[CH3:33]

Participants

6

Reactant 4

HCID 7222BenzothiazoleHCID 25517Ammonium ChlorideHCID 10958318HCID 10958318, compoundHCID 178418339Butyllithium

Product 1

HCID 18518681HCID 18518681, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To benzothiazole (83.3 mg, 2.0 eq) in anhydrous THF (2 mL) under a nitrogen atmosphere and with stirring was added n-BuLi (0.40 mL, 2.0 eq, 1.53 M in hexanes) at −78° C. (bath temperature). The resulting bright yellow coloured reaction mixture was stirred for 1 hour after which 1-(2-diethylaminoethyl)-4-bromoisatin (100.0 mg, 3.08×10−4 mol) in anhydrous THF (2 mL) was added dropwise. The resulting red coloured solution was stirred at −78° C. for 7.5 hours. Saturated aqueous NH4Cl (1.5 mL) was added and the reaction mixture was allowed to warm to room temperature. The mixture was extracted with EtOAc and the combined extracts were dried (anhydrous Na2SO4). After filtration the solvent was removed in vacuo. Purification was carried out by column chromatography (silica gel, eluting 1% to 3% MeOH in CHCl3) to give the title compound as a light yellow solid (20.7 mg, 15%).

Workup

  1. customreaction mixture
  2. additionwas added dropwise
  3. temperatureto warm to room temperature
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialthe combined extracts were dried (anhydrous Na2SO4)
  6. filtrationAfter filtration the solvent
  7. customwas removed in vacuo
  8. customPurification
  9. washwas carried out by column chromatography (silica gel, eluting 1% to 3% MeOH in CHCl3)

Sources & evidence

ORD record
ord-b9af7746b7be4330a20c094bea3ed0f4
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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