Carbon tetrabromide → HCID 18919330, compound

HRID 1291428Notes

Reaction equation

HRID 1291428 reaction equation
O[CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([C:11]2[CH:31]=[CH:30][C:14]([CH2:15][S:16][C:17]3[N:26]([CH3:27])[C:25](=[O:28])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][C:23]=4[CH3:29])[N:18]=3)=[CH:13][CH:12]=2)=[O:10])[CH2:5][CH2:4]1.C(Br)(Br)(Br)[Br:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:33][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([C:11]2[CH:31]=[CH:30][C:14]([CH2:15][S:16][C:17]3[N:26]([CH3:27])[C:25](=[O:28])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][C:23]=4[CH3:29])[N:18]=3)=[CH:13][CH:12]=2)=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18918806HCID 18918806, compound

Product 1

HCID 18919330HCID 18919330, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (25 ml) was dissolved 2-[4-(4-hydroxymethylpiperidylcarbonyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone (1.081 g) followed by addition of carbon tetrabromide (1.050 g). Then, triphenylphosphine (982 mg) was added over 10 minutes and the mixture was stirred at room temperature for 2 hours. The salt was filtered off and the filtrate was concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate =1:1) and rinsed with ether to provide the title compound as colorless solid (496 mg).

Workup

  1. filtrationThe salt was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate =1:1)
  4. washrinsed with ether

Sources & evidence

ORD record
ord-1dc78b2e5b194608847d283f970eacac
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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