Carbon tetrabromide → HCID 23499507, compound

HRID 1836334Notes

Reaction equation

HRID 1836334 reaction equation
[CH2:1]([S:8]([NH:11][NH:12][C:13]1[C:14](=[O:24])[N:15]([CH2:20][CH2:21][CH2:22]O)[C:16]([CH3:19])=[CH:17][N:18]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:1]([S:8]([NH:11][NH:12][C:13]1[C:14](=[O:24])[N:15]([CH2:20][CH2:21][CH2:22][Br:26])[C:16]([CH3:19])=[CH:17][N:18]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 23499504HCID 23499504, compound2×

Product 1

HCID 23499507HCID 23499507, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 3-(2-benzylsulfonylhydrazino)-1-(3-hydroxypropyl)-6-methylpyrazinone, the product of Example 31 (0.429 g, 0.82 mmol) and carbon tetrabromide (0.328 g, 0.99 mmol) in dichloromethane (10 mL), is added triphenylphosphine (0.26 g, 0.99 mmol) portionwise with ice-bath cooling. After the addition is complete, the mixture is stirred for about an additional 2 hours. The solvent is removed in vacuo. The residue is purified by silica gel column chromatography using ethyl acetate/n-hexane as eluent to afford the title compound.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. customThe solvent is removed in vacuo
  4. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b9e0912b8d8844948d27b8e2d0d41d2b
Source dataset
uspto-grants-2004_08
Patent number
US06777431B2

Reaction notes

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