Water → HCID 25064373, compound

HRID 909400Notes

Reaction equation

HRID 909400 reaction equation
[Cl:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7]([OH:10])=[N:8][O:9][C:5]=2[CH:4]=1.[C:13]1([C:19](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1.O>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[N:8]([C:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6456Trityl chlorideHCID 178518985HCID 178518985, compound

Product 1

HCID 25064373HCID 25064373, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 50 mL of methylene chloride, 5.00 g of 6-(chloromethyl)-1,2-benzisoxazol-3-ol, 7.59 g of triphenylmethyl chloride and 2.20 mL of pyridine were suspended and stirred for 5 hours at room temperature. To the reaction mixture, 15 mL of water and 15 mL of methylene chloride were added, and the result was stirred for 5 minutes under reflux and heating. After cooling the reaction mixture, 2.50 g of silica gel was added. After insoluble matter was filtered off, the cake was washed with 10 mL of methylene chloride. The filtrate and the washing solution were combined and, after adding 8 mL of methylene chloride and 15 mL of water, 45 mL of solvent was distilled off under atmospheric pressure. To the reaction mixture, 35 mL of acetone was added and 33 mL of solvent was distilled off under atmospheric pressure. After adding 20 mL of water, solids were filtered and 11.3 g of 6-(chloromethyl)-2-triphenylmethyl-1,2-benzisoxazol-3(2H)-one was obtained in the form of a pale yellowish-white solid.

Workup

  1. stirringthe result was stirred for 5 minutes
  2. temperatureunder reflux
  3. temperatureheating
  4. temperatureAfter cooling the reaction mixture, 2.50 g of silica gel
  5. additionwas added
  6. filtrationAfter insoluble matter was filtered off
  7. washthe cake was washed with 10 mL of methylene chloride
  8. additionafter adding 8 mL of methylene chloride and 15 mL of water, 45 mL of solvent
  9. distillationwas distilled off under atmospheric pressure
  10. additionTo the reaction mixture, 35 mL of acetone was added
  11. distillation33 mL of solvent was distilled off under atmospheric pressure
  12. additionAfter adding 20 mL of water, solids
  13. filtrationwere filtered

Sources & evidence

ORD record
ord-45ecfa031d174a4e878d77a759dccf39
Source dataset
uspto-grants-2011_09
Patent number
US08017789B2

Reaction notes

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