Methanol → HCID 13106724, compound

HRID 1164152Notes

Reaction equation

HRID 1164152 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([Br:12])[CH:9]=[C:8]([Br:13])[C:3]=1[NH:4][N+:5]([O-:7])=[O:6].[OH-].[Na+].CO.Br[CH2:19][C:20]#[CH:21]>O>[Br:1][C:2]1[CH:11]=[C:10]([Br:12])[CH:9]=[C:8]([Br:13])[C:3]=1[N:4]([N+:5]([O-:7])=[O:6])[CH2:21][C:20]#[CH:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 13787593HCID 13787593, compound

Product 1

HCID 13106724HCID 13106724, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,4,6-tribromo-N-nitroaniline (5.0 g; 0.01334 mol) is reacted with a methanolic solution of sodium hydroxide (0.53 g; 0.01324 mol) in the presence of methanol (60 ml). The solvent is then removed, and the residue dried. The thus obtained sodium salt is dissolved in dimethyl sulfoxide (DMSO) and reacted with 3-bromopropyne (1.52 g; 0.0147 mol) at 25° C. The reaction mixture is stirred 16 hours and then poured into water. The title product is extracted with ether (3×125 ml), the combined extract washed with water, dilute sodium hydroxide, water and brine. The ethereal solution is then dried over magnesium sulfate and the solution concentrated to afford the product, mp. 58°-58.5° C.

Workup

  1. customThe solvent is then removed
  2. customthe residue dried
  3. dissolutionThe thus obtained sodium salt is dissolved in dimethyl sulfoxide (DMSO)
  4. extractionThe title product is extracted with ether (3×125 ml)
  5. extractionthe combined extract
  6. washwashed with water, dilute sodium hydroxide, water and brine
  7. dry with materialThe ethereal solution is then dried over magnesium sulfate
  8. concentrationthe solution concentrated
  9. customto afford the product, mp. 58°-58.5° C.

Sources & evidence

ORD record
ord-00a553a0bb0a426aa4445211701c3458
Source dataset
uspto-grants-1983_01
Patent number
US04367339

Reaction notes

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