1,2-Dichloroethane → HCID 4415129, compound

HRID 383983Notes

Reaction equation

HRID 383983 reaction equation
C1C=NC2N(O)N=NC=2C=1.[F:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][CH2:17][NH2:18])=[CH:14][CH:13]=1.[C:21](O)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(Cl)CCl>C(Cl)Cl>[F:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][CH2:17][NH:18][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 4653p-FluorophenethylamineHCID 181649HOAt

Product 1

HCID 4415129HCID 4415129, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.5 g (10.8 mmol) of HOAt were added to a solution of 15.0 g (108.0 mmol) of 4-fluorophenethylamine and 13.2 g (108.0 mmol) of benzoic acid in DCM and the mixture was then cooled to 0° C. 22.8 g (119.0 mmol) of EDC were then added at this temperature and the mixture was then stirred for 16 h at RT. The reaction solution was then washed successively with a 1M aqueous hydrochloric acid (2×300 ml), a 2M aqueous NaOH solution (300 ml) and brine (200 ml). The organic phase was dried over Na2SO4, filtered and concentrated to small volume under vacuum. 20.5 g (84.2 mmol, 78%) of N-(4-fluorophenethyl)benzamide were obtained as the residue.

Workup

  1. washThe reaction solution was then washed successively with a 1M aqueous hydrochloric acid (2×300 ml)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-e8b30a8aca7a4a76b1dfa733f16b4ddc
Source dataset
uspto-grants-2013_02
Patent number
US08367700B2

Reaction notes

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