Hydrochloric Acid → HCID 68765118, compound

HRID 1615755Notes

Reaction equation

HRID 1615755 reaction equation
Cl.Cl.[F:3][C:4]1[CH:5]=[C:6]([CH:10]([NH2:13])[CH2:11][NH2:12])[CH:7]=[CH:8][CH:9]=1.[OH-:14].[Na+].[O:16]1[CH2:22][C:21](=O)[CH2:20][O:19][CH2:18][CH2:17]1.[CH:24](Cl)(Cl)Cl.Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[F:3][C:4]1[CH:5]=[C:6]([CH:10]2[NH:13][C:24](=[O:14])[C:21]3([CH2:22][O:16][CH2:17][CH2:18][O:19][CH2:20]3)[NH:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 22756585HCID 22756585, compoundHCID 468563761,4-Dioxepan-6-one

Product 1

HCID 68765118HCID 68765118, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

0.47 g (2.1 mmol) 1-(3-fluorophenyl)ethan-1,2-diamine dihydrochloride were placed with 23 mg (0.10 mmol) benzyltriethylammonium chloride in 50 ml dichloromethane and cooled with ice/acetone. Then 0.71 ml (14 mmol) of a 50% sodium hydroxide solution were added. At 0° C. 0.23 g (2 mmol) [1,4]dioxepan-6-one were added dropwise together with 0.24 ml (4.6 mmol) chloroform and 20 ml dichloromethane. The mixture was left overnight to warm up to RT. Then the reaction mixture was cooled to 0° C. and adjusted to pH 1 with a 6N aqueous hydrochloric acid solution. The phases were separated. The aqueous phase was made alkaline with a 4N sodium hydroxide solution and extracted with DCM. The combined organic phases were dried and evaporated to dryness by rotary evaporation.

Workup

  1. customAt 0° C
  2. temperatureThen the reaction mixture was cooled to 0° C.
  3. customThe phases were separated
  4. extractionextracted with DCM
  5. customThe combined organic phases were dried
  6. customevaporated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-89485050edc744d1bf35e077d916c0e3
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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