Hydrogen Bromide → HCID 68700711, compound

HRID 1865803Notes

Reaction equation

HRID 1865803 reaction equation
[Br:1][CH2:2][CH2:3][N:4]([CH2:22][CH2:23][Br:24])[C:5]1[C:6]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:7][C:8]([N+:15]([O-:17])=[O:16])=[C:9]([CH:14]=1)[C:10]([O:12]C)=[O:11].[OH-].[K+].Br>O1CCOCC1.CO>[Br:1][CH2:2][CH2:3][N:4]([CH2:22][CH2:23][Br:24])[C:5]1[C:6]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:7][C:8]([N+:15]([O-:17])=[O:16])=[C:9]([CH:14]=1)[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14797Potassium HydroxideHCID 68702921HCID 68702921, compound

Product 1

HCID 68700711HCID 68700711, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 6 (1.00 g, 2.05 mmol) in a dioxane/MeOH (1:1, 20 mL) was treated at 10° C. with 4N aqueous KOH (5 mL), and stirred at 10° C. for 45 min. The mixture was acidified to pH 2 with1 N aqueous HBr, concentrated to a small volume under reduced pressure, and then diluted with saturated aqueous NaBr (20 mL). The resulting semi-solid was isolated and crystallized twice from MeOH/H2O to give 5-[bis(2-bromoethyl)amino]-4-(methylsulfonyl)-2-nitrobenzoic acid (7) (0.70 g, 72%): mp 174-176° C.; 1H NMR [(CD3)2SO] δ 8.50 (s, 1 H), 7.88 (s, 1 H), 3.79 (t, J=7.0 Hz, 4 H), 3.62 (t, J=7.0 Hz, 4 H), 3.48 (s, 3 H). Anal. (C12H14Br2N2O6S) C, H, N.

Workup

  1. concentrationconcentrated to a small volume under reduced pressure
  2. additiondiluted with saturated aqueous NaBr (20 mL)
  3. customThe resulting semi-solid was isolated
  4. customcrystallized twice from MeOH/H2O

Sources & evidence

ORD record
ord-25671ca5cdb545089aee45864ecfd684
Source dataset
uspto-grants-2009_12
Patent number
US07629332B2

Reaction notes

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