Methylamine → HCID 44481362, compound

HRID 452403Notes

Reaction equation

HRID 452403 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=[CH:12][C:6]=2[CH2:5][O:4]1.[CH3:17][NH2:18]>CCO>[CH3:17][NH:18][CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=[CH:12][C:6]=2[CH2:5][O:4]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 668864402-(bromomethyl)-7-(methylsulfonyl)-4H-1,3-benzodioxine

Product 1

HCID 44481362HCID 44481362, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 2-(bromomethyl)-7-(methylsulfonyl)-4H-1,3-benzodioxine (0.4 g, 1.30 mmol), methanamine (33% in EtOH, 2.0 ml, 16.1 mmol) and EtOH (3.0 ml) was heated in a micro wave oven at 145° C. for 30 min. The volatiles were evaporated in vacuum and the crude product was chromathographed twice on a silica column using EtOAc/MeOH (4:1) as eluent. Collection of the fractions containing pure product and evaporation of the solvent afforded the title compound (0.25 g, 74%). The amine was converted into hydrochloric acid salt and crystallized from EtOH/MeOH/DEE. M.p. 225° C. MS m/z (rel. intensity, 70 eV) 257 (M+, 1), 123 (76), 78 (35), 77 (bp), 51 (97).

Workup

  1. customThe volatiles were evaporated in vacuum
  2. customCollection of the fractions
  3. additioncontaining pure
  4. customproduct and evaporation of the solvent

Sources & evidence

ORD record
ord-6912a236193241788d5374093848ce31
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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