Phosphorus oxychloride → HCID 86722265, compound

HRID 869419Notes

Reaction equation

HRID 869419 reaction equation
O[C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[C:10]([NH:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[S:11][CH:12]=2)[N:5]=[C:4]2[C:19]3[C:25]([Br:26])=[C:24]([O:27][CH3:28])[CH:23]=[CH:22][C:20]=3[O:21][C:3]=12.O=P(Cl)(Cl)[Cl:31]>>[Br:26][C:25]1[C:19]2[C:4]3[C:3]([O:21][C:20]=2[CH:22]=[CH:23][C:24]=1[O:27][CH3:28])=[C:2]([Cl:31])[CH:7]=[C:6]([C:8]1[N:9]=[C:10]([NH:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[S:11][CH:12]=1)[N:5]=3

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178488263HCID 178488263, compound

Product 1

HCID 86722265HCID 86722265, compoundYield 27%

Conditions

Temperature
110 °C

Procedure

A mixture of 16C (0.7 g, 1.5 mmol) in POCl3 (10 mL) was heated to 110° C. and reacted for 30 min. TLC monitored the reaction. After the reaction completed, POCl3 in the reaction mixture was evaporated. The residue was added dropwise into ice-water. The precipitated solids were collected by filtration and purified by short column chromatography to give M16 (0.2 g, 27% yield).

Workup

  1. customreacted for 30 min
  2. customthe reaction
  3. customPOCl3 in the reaction mixture was evaporated
  4. additionThe residue was added dropwise into ice-water
  5. filtrationThe precipitated solids were collected by filtration
  6. custompurified by short column chromatography
  7. customto give M16 (0.2 g, 27% yield)

Sources & evidence

ORD record
ord-8d03593fb0824a0f883d9221e39430c9
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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