Water → HCID 19601662, compound

HRID 610642Notes

Reaction equation

HRID 610642 reaction equation
[I:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][CH:7]([CH3:16])[CH:8](O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O>ClC1C=CC=CC=1Cl>[I:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([CH3:16])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14812Phosphorus oxide (P4O10)HCID 54110010HCID 54110010, compound

Product 1

HCID 19601662HCID 19601662, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of amide 3a, 9.5 g, 24.9 mmol) and P2O5 (44 g) in o-dichlorobenzene (150 mL) was refluxed for overnight. 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 (6.68 g, 80%). mp 111-112° C. 1H NMR (CDCl3) d 2.67 (s, 3 H, CH3), 7.00-7.05 (m, 1 H, aromatic), 7.26-7.52 (m, 6 H, aromatic), 7.65 (d, J=8.1 Hz, 1 H, aromatic), 7.88 (d, J=8.1 Hz, 1 H, aromatic). 13C NMR (CDCl3) d 24.05 (q, CH3), 97.82 (s, =CI--, aromatic), 118.26 (d, aromatic), 124.45 (s, aromatic), 125.98 (d, aromatic), 126.77 (d, aromatic), 127.70 (d, aromatic), 129.43 (d, aromatic), 129.79 (d, aromatic), 129.92 (d, aromatic), 136.73 (s, aromatic), 138.78 (d, aromatic), 143.74 (s, aromatic), 150.24 (s, aromatic), 161.34 (s, =CCH3 --, aromatic). Anal. Calcd for C16H12IN: C, 55.67; H, 3.50; N, 4.06. Found: C, 55.77; H, 3.51; N, 3.96.

Workup

  1. temperaturewas refluxed for overnight
  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-befa3b59b25a472d99dc39c6409edf26
Source dataset
uspto-grants-1999_12
Patent number
US05998624

Reaction notes

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