Diethylamine → HCID 70979643, compound

HRID 2271334Notes

Reaction equation

HRID 2271334 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[C:7]([F:15])[CH:6]=1.[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17]>C(O)C>[CH2:16]([N:18]([CH2:19][CH3:20])[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[C:7]([F:15])[CH:6]=1)[CH3:17]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86717739HCID 86717739, compound

Product 1

HCID 70979643HCID 70979643, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation according to Example 1 but performed in one portion: 1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene (0.5 g, 1.68 mmol) and di-ethylamine (1.39 ml, 13.46 mmol) in ethanol (4 ml). Purification by flash column chromatography (ethyl acetate/methanol, 1:0 to 1:1) gave the title compound (300 mg, 61.6%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 172.3° C. MS m/z (relative intensity, 70 eV) 289 (M+, 1), 274 (6), 87 (6), 86 (bp), 58 (5).

Workup

  1. customPreparation
  2. customPurification by flash column chromatography (ethyl acetate/methanol, 1:0 to 1:1)

Sources & evidence

ORD record
ord-98903a7157c04e8bafdaf51c9456d308
Source dataset
uspto-grants-2015_09
Patent number
US09120728B2

Reaction notes

Loading…