Dichloromethane → HCID 70980365, compound

HRID 2271339Notes

Reaction equation

HRID 2271339 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.[NH:16]1[CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>C(#N)C>[F:15][C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=1)[O:4][CH2:3][CH2:2][N:16]1[CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10422AzetidineHCID 11430Potassium CarbonateHCID 86717739HCID 86717739, compound

Product 1

HCID 70980365HCID 70980365, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene (0.5 g, 1.6 mmol), azetidine (0.23 ml, 3.2 mmol) and potassium carbonate (0.58 g, 4.2 mmol) was dissolved in acetonitrile (10 ml). The mixture was heated in a sealed container at 120° C. for 2 h. The reaction mixture was cooled to room temperature, CH2Cl2 (100 ml) was added, solids was filtered off and the volatiles were evaporated. The amine was converted to the fumaric acid salt and re-crystallized from methanol/diethyl ether. MS m/z (relative intensity, 70 eV) 273 (M+, 1), 94 (5), 82 (3), 71 (5), 70 (bp).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationsolids was filtered off
  3. customthe volatiles were evaporated
  4. customre-crystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-c486dd16e6c14a00b2e48518359803fe
Source dataset
uspto-grants-2015_09
Patent number
US09120728B2

Reaction notes

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