Ethylamine → HCID 44481626, compound

HRID 452406Notes

Reaction equation

HRID 452406 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[C:10]([S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH:11]=[CH:12][C:6]=2[CH2:5][O:4]1.[CH2:20]([NH2:22])[CH3:21]>C(#N)C>[F:17][C:16]([F:19])([F:18])[S:13]([C:10]1[CH:11]=[CH:12][C:6]2[CH2:5][O:4][CH:3]([CH2:2][NH:22][CH2:20][CH3:21])[O:8][C:7]=2[CH:9]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 67155666HCID 67155666, compound

Product 1

HCID 44481626HCID 44481626, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 9. 2-(bromomethyl)-7-[(trifluoromethyl)sulfonyl]-4H-1,3-benzodioxine (0.28 g, 0.76 mmol), ethanamine (70% in water, 2.0 ml, 25.2 mmol) and ACN (2.0 ml) was heated at 120° C. for 20 min. Purification by flash chromatography using EtOAc/MeOH (4:1) as eluent afforded the title compound (0.14 g, 52%). The amine was converted into hydrochloric acid salt and crystallized from EtOH/DEE. M.p. 169° C. MS m/z (rel. intensity, 70 eV) 325 (M+, 1), 239 (5), 106 (5), 77 (7), 58 (bp).

Workup

  1. customPreparation
  2. customPurification by flash chromatography

Sources & evidence

ORD record
ord-da3c8587ada4460681eb039fcfacbffa
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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