Phosphorus oxychloride → HCID 53913829, compound

HRID 2293479Notes

Reaction equation

HRID 2293479 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]([NH2:16])=O)=[CH:10][C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]#[N:16])=[CH:10][C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 53898074HCID 53898074, compound

Product 1

HCID 53913829HCID 53913829, compoundYield 42.4%

Conditions

Temperature
100 °C

Procedure

A mixture of 75 mg (0.20 mMol) of the product of Example 21 and 5 ml of POCl3 was heated to 100° C. for 2 hours, cooled to room temperature, poured into ice-water and extracted with dichloromethane (4×15 ml). The combined organic layers were extracted once with brine, dried over MgSO4 and evaporated to dryness to recover a colorless oil. Trituration with ether gave a colorless solid which was dried at 0.1 mm Hg at 50° C. to give 29.9 mg (42%) of solid: m.p. 178°-181.5° C.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with dichloromethane (4×15 ml)
  3. extractionThe combined organic layers were extracted once with brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customto recover a colorless oil
  7. customTrituration with ether gave a colorless solid which
  8. customwas dried at 0.1 mm Hg at 50° C.

Sources & evidence

ORD record
ord-f543da71c2f04c1d96fa579df847bc0d
Source dataset
uspto-grants-1997_11
Patent number
US05686470

Reaction notes

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