Phosphorus oxychloride → HCID 68194425, compound

HRID 2370613Notes

Reaction equation

HRID 2370613 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13]([S:19][CH3:20])=[N:14][CH:15]=2)[NH:10][C:9]1=O.O=P(Cl)(Cl)[Cl:24].C(N(C(C)C)CC)(C)C>>[Cl:24][C:9]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:17](=[O:18])[C:16]2[C:11]([N:10]=1)=[N:12][C:13]([S:19][CH3:20])=[N:14][CH:15]=2

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 68194364HCID 68194364, compound

Product 1

HCID 68194425HCID 68194425, compound

Procedure

A mixture of Example 1A (15.9 g, 49.6 mmol) in POCl3 (55 ml, 590 mmol) and diisopropylethylamine (55 ml, 315 mmol) was heated at 90° C. for 1.5 hours. The reaction mixture was concentrated. The residue was treated with ice and saturated NaHCO3 carefully and then extracted with ethyl acetate. The insoluble material suspended in the two layers was filtered, washed with ether and water, and oven dried to provide the title compound. The two layers in the filtrate were separated. The aqueous layer was washed with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, concentrated, and triturated (twice) with ethyl acetate/ether to provide additional title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was treated with ice and saturated NaHCO3 carefully
  3. extractionextracted with ethyl acetate
  4. filtrationwas filtered
  5. washwashed with ether and water, and oven
  6. customdried

Sources & evidence

ORD record
ord-73562082e05348f6a913be00b9dfd6b9
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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