Hydrogen Bromide → HCID 68831940, compound

HRID 1784402Notes

Reaction equation

HRID 1784402 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:22]([O:23]C)=[CH:21][C:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19][C:13]=3[CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[BrH:25]>>[BrH:25].[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[C:22]([OH:23])=[CH:21][C:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19][C:13]=3[CH:12]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 57592471HCID 57592471, compound

Product 1

HCID 68831940HCID 68831940, compound

Procedure

A solution of D5 (300 mg, 0.86 mmol) in aqueous 48% HBr (10 mL) was heated at 120° C. overnight. The mixture was cooled to room temperature and the solvent removed, azeotroping with toluene. Diethyl ether was added to the residue to yield the title compound D6 as the hydrobromide salt (340 mg). MH+ 336. 1H NMR δ (DMSO-d6) 2.75 (3H, d), 2.88-3.25 (6H, m), 3.50-3.66 (2H, m), 7.35-7.50 (2H, t), 7.76 (1H, s), 7.90-8.03 (2H, m), 9.85 (1H, br.s), 10.80 (1H, br.s).

Workup

  1. customthe solvent removed
  2. customazeotroping with toluene
  3. additionDiethyl ether was added to the residue

Sources & evidence

ORD record
ord-4f8d102d083941a48b12fa9e1bf0b32b
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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