Phenylacetyl chloride → HCID 15231960, compound

HRID 274808Notes

Reaction equation

HRID 274808 reaction equation
[NH2:1][CH:2]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:3]([NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:30]1([CH2:36][C:37](Cl)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>ClCCl>[C:24]1([CH:2]([NH:1][C:37](=[O:38])[CH2:36][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][CH:15]=2)=[O:12])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 15231944HCID 15231944, compound

Product 1

HCID 15231960HCID 15231960, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [R-(R*,R*)] and [S-(R*,R*)]-N-(2-amino-1,2-diphenylethyl)-N'-[4-(trifluoromethyl)phenyl]urea (0.1 g, 0.25 mmol) in dichloromethane (5 mL) is added phenylacetyl chloride (0.05 g, 0.3 mmol) followed by triethylamine (0.03 g, 0.3 mmol) in one portion. The resulting mixture is stirred 2 hours at room temperature before concentrating in vacuo. The residue is dissolved in diethyl ether and the organic layer washed with aqueous 1N NaOH, aqueous saturated NaCl, and dried over MgSO4. Filtration and concentration gives an oil which is purified by flash chromatography (SiO2, EtOAc/hexane eluent). The resulting solid is recrystallized from ethyl acetate/hexane to give 0.07 g (52%) of desired white solid, mp 233.5°-234° C. NMR (DMSO-d6): 3.46 (dd, 2H, J=26.4, 14 Hz), 5.10 (m, 2H), 6.97-7.19 (m, 20H), 7.57 (s, 4H), 8.82 (d, 1H, J=8.3 Hz), 8.98 (s, 1H). Analysis calculated for C30H26F3N3O2.0.71H2O: C, 67.94; H, 5.21; N, 7.92. Found: C, 67.94; H, 4.84; N, 7.86.

Workup

  1. concentrationbefore concentrating in vacuo
  2. dissolutionThe residue is dissolved in diethyl ether
  3. washthe organic layer washed with aqueous 1N NaOH, aqueous saturated NaCl
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration
  6. customgives an oil which
  7. customis purified by flash chromatography (SiO2, EtOAc/hexane eluent)
  8. customThe resulting solid is recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1dd94aedcec64c8486f0b94d51fde212
Source dataset
uspto-grants-1995_02
Patent number
US05389682

Reaction notes

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