Water → HCID 15870107, compound

HRID 1698840Notes

Reaction equation

HRID 1698840 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH2:10].C(N(CC)CC)C.[C:18]([C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][N:10]1[C:18]([OH:25])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:26]2[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:28]1=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 6433572-(2-Fluorophenyl)ethylamineHCID 109992952-benzoylbenzoyl chloride

Product 1

HCID 15870107HCID 15870107, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

At room temperature, 0.31 g (2.2 mmol) of 2-(2-fluorophenyl)ethylamine and 0.22 g (2.2 mmol) of triethylamine in 10 ml of absolute toluene were admixed dropwise with a solution of 0.49 g (2.0 mmol) of 2-benzoylbenzoyl chloride in 10 ml of absolute toluene. The reaction mixture was heated under eflux for 3 h. After cooling, the turbid solution was admixed with 20 ml of water. The organic phase was separated off, diluted with 20 ml of toluene and washed three times with 1 M hydrochloric acid. To complete the extraction, the combined aqueous phases were extracted with diethyl ether. The combined organic phases were washed three times with 1 M aqueous sodium hydroxide solution and once with saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness using a rotary evaporator. The residue was recrystallized from toluene. The resulting colorless crystalline product was filtered off with suction and dried. Yield: 53 g. M.p.: 208° C.

Workup

  1. customAt room temperature
  2. temperatureThe reaction mixture was heated under eflux for 3 h
  3. temperatureAfter cooling
  4. customThe organic phase was separated off
  5. additiondiluted with 20 ml of toluene
  6. washwashed three times with 1 M hydrochloric acid
  7. extractionthe extraction
  8. extractionthe combined aqueous phases were extracted with diethyl ether
  9. washThe combined organic phases were washed three times with 1 M aqueous sodium hydroxide solution
  10. dry with materialonce with saturated sodium chloride solution, dried over sodium sulfate
  11. customevaporated to dryness
  12. customa rotary evaporator
  13. customThe residue was recrystallized from toluene
  14. filtrationThe resulting colorless crystalline product was filtered off with suction
  15. customdried

Sources & evidence

ORD record
ord-6322499964a44901bdc6f24a89f375a7
Source dataset
uspto-grants-2002_02
Patent number
US06344468B1

Reaction notes

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