Phosphorus oxychloride → HCID 86691626, compound

HRID 624318Notes

Reaction equation

HRID 624318 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:11]2[CH:12]=[C:13]([O:19][CH:20]([CH3:22])[CH3:21])[C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:10]=2[O:9][C:8]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=O.O=P(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[F:29][C:26]1[CH:25]=[CH:24][C:23]([C:8]2[O:9][C:10]3[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[C:13]([O:19][CH:20]([CH3:21])[CH3:22])=[CH:12][C:11]=3[C:7]=2[C:5]2[NH:4][CH2:3][CH2:2][N:1]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86691627HCID 86691627, compound

Product 1

HCID 86691626HCID 86691626, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(2-aminoethyl)-2-(4-fluorophenyl)-5-isopropoxy-6-nitrobenzofuran-3-carboxamide (1.2 g, 2.99 mmol) in toluene (75 mL) at room temperature under nitrogen was added POCl3 (2.79 mL, 29.9 mmol). The reaction mixture was heated to 100° C. and maintained at same temperature overnight. The reaction mixture was concentrated completely under vacuum, and the residue diluted with water, basified with NaHCO3. The product was extracted with EtOAc (100 mL×3), washed with brine, dried over Na2SO4 and concentrated to obtain 2-(2-(4-fluorophenyl)-5-isopropoxy-6-nitrobenzofuran-3-yl)-4,5-dihydro-1H-imidazole as a yellow solid. Yield: 1.0 g (87%). LCMS: (ES+) m/z=384.28 (M+H)+; Column—ACQUITY UPLC BEH C8 (50×2.1 mm; 1.7 nm); M phase A: 5 mM Ammonium Acetate:MeCN (95:5); M phase B: 5 mM Ammonium Acetate:MeCN (5:95)

Workup

  1. temperaturemaintained at same temperature overnight
  2. concentrationThe reaction mixture was concentrated completely under vacuum
  3. additionthe residue diluted with water
  4. extractionThe product was extracted with EtOAc (100 mL×3)
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-452089c4b7ab48fdb29e74e092badbd7
Source dataset
uspto-grants-2016_04
Patent number
US09303020B2

Reaction notes

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