Phosphorus pentachloride → HCID 19902182, compound

HRID 2372724Notes

Reaction equation

HRID 2372724 reaction equation
[N:1]1[CH2:2][CH2:3][N:4]2[C:13]=1[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]1[CH:14]=[N:15][C:16]([C:17]([NH2:19])=O)=[C:5]21.P(Cl)(Cl)(Cl)(Cl)Cl>P(Cl)(Cl)(Cl)=O>[C:17]([C:16]1[N:15]=[CH:14][N:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]3=[N:1][CH2:2][CH2:3][N:4]3[C:5]=12)#[N:19]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 19902191HCID 19902191, compound

Product 1

HCID 19902182HCID 19902182, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2,3-dihydrodiimidazo[1,5-a:1',2'-c]quinazoline-5-carboxamide (1 g, 4 mmol) (prepared by standard methods from the corresponding carboxylic acid ethyl ester, Compound 3) and phosphorus pentachloride (0.9 g, 4.1 mmol) in phosphorus oxychloride (10 ml) was stirred at reflux for 3 h, and then evaporated to dryness. The residue was partitioned between 25 ml of water and 25 ml of dichloromethane. The organic layer was extracted with 4×25 ml of 10% acetic acid. The combined aqueous phases were adjusted to pH around 11 and cooled to 0° C. The precipitate which had formed was filtered off and dried, giving the title compound as yellow crystals, m.p. 227°-240° C. (decomposition). Yield 0.53 g (57%). (Compound 49).

Workup

  1. temperatureat reflux for 3 h
  2. customevaporated to dryness
  3. customThe residue was partitioned between 25 ml of water and 25 ml of dichloromethane
  4. extractionThe organic layer was extracted with 4×25 ml of 10% acetic acid
  5. customThe precipitate which had formed
  6. filtrationwas filtered off
  7. customdried

Sources & evidence

ORD record
ord-faf67c0f371246a496940f4f4be12afe
Source dataset
uspto-grants-1992_03
Patent number
US05100895

Reaction notes

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