Water → HCID 19601653, compound

HRID 610643Notes

Reaction equation

HRID 610643 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([NH:7][CH:8]([CH3:17])[CH:9](O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O>ClC1C=CC=CC=1Cl>[I:1][C:2]1[CH:3]=[C:4]([C:5]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]([CH3:17])[N:7]=2)[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14812Phosphorus oxide (P4O10)HCID 53872605HCID 53872605, compound

Product 1

HCID 19601653HCID 19601653, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of amide 3b, 11.54 g, 30.3 mmol) and P2O5 (43 g) in o-dichlorobenzene (150 mL) was refluxed for 20 h. After it was cooled to room temperature, it was cooled to 0° C. by application of an external ice-water bath. To this cooled mixture was cautiously added 300 mL of H2O. After the vigorous reaction had subsided, the dark solution was washed with toluene (2×50 mL). The aqueous layer was cooled to 0° C. and made to pH >11 with 50% aqueous NaOH. The resulting mixture was extracted with toluene (4×50 mL). The organic layers were dried (MgSO4), filtered. The filtrate was concentrated in vacuo. The residue was recrystallized from benzene, thereby affording a white solid (6.5 g, 62%) mp 77-78° C. 1H NMR (CDCl3) d 2.72 (s, 3 H, CH3), 7.23 (t, J=7.8 Hz, 1 H, aromatic), 7.40-7.52 (m, 2 H, aromatic), 7.57-7.66 (m, 2 H, aromatic), 7.71-7.85 (m, 2 H, aromatic), 7.92 (d, J=8.7 Hz, 1 H, aromatic), 8.02 (s, 1 H, aromatic). 13C NMR (CDCl3) d 24.31 (q, CH3), 94.31 (s, =CI--, aromatic), 118.36 (d, aromatic), 126.39 (d, 2C, aromatic), 126.92 (d, aromatic), 129.08 (d, aromatic), 129.83 (d, aromatic), 129.99 (d, aromatic), 137.34 (d, aromatic), 137.47 (s, aromatic), 138.53 (d, aromatic), 141.70 (s, aromatic), 150.80 (s, aromatic), 158.36 (s, =CCH3 --, aromatic). Anal. Calcd for C16H12IN: C, 55.67; H, 3.50; N, 4.06. Found: C, 55.53; H, 3.56; N, 4.05.

Workup

  1. temperaturewas refluxed for 20 h
  2. temperatureit was cooled to 0° C. by application of an external ice-water bath
  3. customAfter the vigorous reaction
  4. washthe dark solution was washed with toluene (2×50 mL)
  5. temperatureThe aqueous layer was cooled to 0° C.
  6. extractionThe resulting mixture was extracted with toluene (4×50 mL)
  7. dry with materialThe organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customThe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-f40c4826c6d24f54a35a26f065b66301
Source dataset
uspto-grants-1999_12
Patent number
US05998624

Reaction notes

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