Water → HCID 22273556, compound

HRID 2375287Notes

Reaction equation

HRID 2375287 reaction equation
[OH:1]OS([O-])=O.[K+].[CH3:7][N:8]([CH2:10][CH2:11][CH2:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)[CH3:9].[OH2:21]>CO>[CH3:7][N:8]([CH2:10][CH2:11][CH2:12][S:13]([C:14]1[CH:15]=[CH:16][C:17]([Br:20])=[CH:18][CH:19]=1)(=[O:1])=[O:21])[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 20572885HCID 20572885, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22273556HCID 22273556, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Oxone (14 g, 23 mmol) was added to a solution of 1-[3-(N,N-dimethylamino) propylthio]-4-bromobenzene (Method 62; 5.24 g, 19.1 mmol) in MeOH (150 ml) and water (30 ml) and the mixture was stirred at ambient temperature for 90 minutes. The reaction mixture was poured onto an Isolute SCX-2 column, washed MeOH (6×40 ml) and the product eluted with 2% methanolic ammonia (10×40 ml). The solvent was evaporated and residue purified by flash chromatography on silica gel eluting with DCM/2% methanolic ammonia (100:0 increasing in polarity to 94:6) to yield the title compound (4.68 g, 80%) as a pale yellow oil. NMR 1.62 (m, 2H), 2.03 (s, 6H), 2.19 (t, 2H), 3.32 (m, 2H), 7.81 (m, 4H); m/z 306.

Workup

  1. additionThe reaction mixture was poured onto an Isolute SCX-2 column
  2. washwashed MeOH (6×40 ml)
  3. washthe product eluted with 2% methanolic ammonia (10×40 ml)
  4. customThe solvent was evaporated
  5. customresidue purified by flash chromatography on silica gel eluting with DCM/2% methanolic ammonia (100:0 increasing in polarity to 94:6)

Sources & evidence

ORD record
ord-151ab165ba064df7b7aa077e61a50cc6
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

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