Chloroform → HCID 15078414, compound

HRID 1110440Notes

Reaction equation

HRID 1110440 reaction equation
[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10](C(=O)CCl)[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2].P([O-])(O)(O)=O.[Na+].ClC1C=CC=[C:27]([C:31]([O:33]O)=[O:32])C=1.C(Cl)(Cl)[Cl:36]>>[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:33][C:31](=[O:32])[CH2:27][Cl:36])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 70297m-Chloroperbenzoic acidHCID 15078413HCID 15078413, compoundHCID 23672064Monosodium phosphate

Product 1

HCID 15078414HCID 15078414, compoundYield 48%

Procedure

To a suspension of 5.03 g of 2-acetylamino-5-chloroacetylindan in chloroform are added 6.8 g of sodium dihydrogenphosphate and 10.06 g of m-chloroperbenzoic acid, and the mixture is refluxed for 5 hours under stirring. The reaction mixture is evaporated to remove solvent and the residue is extracted with ethyl acetate. The extract is washed successively with an aqueous sodium bicarbonate solution and an aqueous 10% hydrochloric acid solution, dried and evaporated to remove solvent. The residue is recrystallized from ethyl acetate-n-hexane-isopropyl ether to give 2.6 g of 2-acetylamino-5-chloroacetoxyindan. Yield: 48%

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. customThe reaction mixture is evaporated
  3. customto remove solvent
  4. extractionthe residue is extracted with ethyl acetate
  5. washThe extract is washed successively with an aqueous sodium bicarbonate solution
  6. dry with materialan aqueous 10% hydrochloric acid solution, dried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue is recrystallized from ethyl acetate-n-hexane-isopropyl ether

Sources & evidence

ORD record
ord-7fc2592090374dba8416c247eb31a2fb
Source dataset
uspto-grants-1990_12
Patent number
US04975460

Reaction notes

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