Hydrochloric Acid → HCID 178439742, compound

HRID 2257011Notes

Reaction equation

HRID 2257011 reaction equation
C([O:5][C:6]([C:8]([CH3:26])=[CH:9][C:10]1[C:11](=[O:25])[C:12]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:13]=2[NH:14][C:15](=[O:19])[C:16]=1[O:17]C)=[O:7])(C)(C)C.B(Br)(Br)Br.C(=O)(O)[O-].[Na+].Cl>C(Cl)Cl>[Cl:24][C:21]1[CH:22]=[CH:23][C:12]2[C:11](=[O:25])[C:10](/[CH:9]=[C:8](\[CH3:26])/[C:6]([OH:7])=[O:5])=[C:16]([OH:17])[C:15](=[O:19])[NH:14][C:13]=2[CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 54536125HCID 54536125, compound

Product 1

HCID 178439742HCID 178439742, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[2-(Tert-butoxycarbonyl)propenyl]-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.32 g) in methylene chloride (4 mL) was added to boron tribromide (0.33 mL) in methylene chloride (4 mL) at room temperature under argon. The mixture was stirred at room temperature for 1.5 hours and then it was added to saturated aqueous sodium bicarbonate (24 mL). The mixture was stirred for 10 minutes and then it was acidified to pH 5 with concentrated hydrochloric acid. The suspension was cooled to -10° C. and the solid was filtered off, washed with water, and vacuum dried to give a white solid (0.16 g). The solid was dissolved in hot methanol (60 mL), filtered, and concentrated to 10 mL volume. The suspension was cooled in an ice bath and the solid was filtered off, washed with cold methanol, and vacuum dried to give a white solid (0.1051 g); mp=242.2°-243.0° C. (dec); 1H NMR (d6 :DMSO) 7.48 (s,1) for olefin proton; MS: m/z=264, 290, 308 (M+1). Analysis for C14H10ClNO5 : Calculated: C, 54.65; H, 3.28; N, 4.55; Found: C, 54.85; H, 3.48; N, 4.50.

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. temperatureThe suspension was cooled to -10° C.
  3. filtrationthe solid was filtered off
  4. washwashed with water, and vacuum
  5. customdried

Sources & evidence

ORD record
ord-096abb4672e94d549e47b9ed29c089eb
Source dataset
uspto-grants-1997_08
Patent number
US05656626

Reaction notes

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