Phosphorus oxychloride → HCID 178432314, compound

HRID 263722Notes

Reaction equation

HRID 263722 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]2[N:23]=[C:24]([CH3:30])[N:25](C(C)(C)C)[C:4]=2[C:3]=1[CH3:31].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]2[N:23]=[C:24]([CH3:30])[NH:25][C:4]=2[C:3]=1[CH3:31]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 53752236HCID 53752236, compound

Product 1

HCID 178432314HCID 178432314, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The material from Example 32 was diluted with toluene then combined with phosphorous oxychloride and heated at reflux overnight. The reaction mixture was concentrated under vacuum. The residue was diluted with water, basified with ammonium hydroxide then extracted several times with methylene chloride. The methylene chloride extracts were combined, dried over magnesium sulfate then concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with 10-40% ethyl acetate in hexane to provide the desired product.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additionThe residue was diluted with water
  5. extractionthen extracted several times with methylene chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationthen concentrated under vacuum
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with 10-40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ae60d27a718c44d08a00d2b50f2bbbf6
Source dataset
uspto-grants-1997_07
Patent number
US05644063

Reaction notes

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