Formic Acid → HCID 13656090, compound

HRID 745986Notes

Reaction equation

HRID 745986 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][S:6][C:7]1[CH:22]=[CH:21][C:10]2[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])=[N:12][O:13][C:9]=2[C:8]=1[Cl:23])[CH3:2].OO.C(O)=[O:28].C(Cl)Cl>O>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][S:6]([C:7]1[CH:22]=[CH:21][C:10]2[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])=[N:12][O:13][C:9]=2[C:8]=1[Cl:23])=[O:28])[CH3:2]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 6344DichloromethaneHCID 13015743HCID 13015743, compound

Product 1

HCID 13656090HCID 13656090, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.0g (8.2 mmole) of ethyl[[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]thio]acetate, 2.5g of a 30% H2O2 solution, 10 ml of formic acid and 50 ml of CH2Cl2 was stirred at room temperature for two hours. The reaction was diluted with water and extracted three times with CH2Cl2. The organics were combined, washed with dilute NaHCO3 and dried over MgSO4. The solution was concentrated at reduced pressure to a yellow oil which solidified to a cream-colored solid, 3.0g (94%) of ethyl[[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]sulfinyl]acetate, m.p. 115°-118° C. The solid was recrystallized from ether to afford pale yellow prisms of ethyl[[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]sulfinyl]acetate, m.p. 120°-121° C.

Workup

  1. extractionextracted three times with CH2Cl2
  2. washwashed with dilute NaHCO3
  3. dry with materialdried over MgSO4
  4. concentrationThe solution was concentrated at reduced pressure to a yellow oil which
  5. customThe solid was recrystallized from ether

Sources & evidence

ORD record
ord-d6201f67c16145d89adaf71aee30c713
Source dataset
uspto-grants-1986_07
Patent number
US04602028

Reaction notes

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