Hydrochloric Acid → HCID 13557219, compound

HRID 1583477Notes

Reaction equation

HRID 1583477 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8]C(OCC)=O)[CH:5]=[CH:4][C:3]=1[CH2:14][N:15]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[CH2:17][O:16]1.I[Si](C)(C)C.Cl>C(Cl)(Cl)Cl>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:14][N:15]2[C:19](=[O:20])[C:18]([CH3:21])([CH3:22])[CH2:17][O:16]2)=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 85247Trimethylsilyl iodideHCID 13557218HCID 13557218, compound

Product 1

HCID 13557219HCID 13557219, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of 8.4 grams (0.026 mole) of 2-[2-chloro-4-(ethoxycarbonylamino)phenyl]methyl-4,4-dimethyl-3-isoxazolidinone in 100 ml of chloroform, under an argon atmosphere and at ambient temperature, was carefully added dropwise 6.0 grams (0.03 mole) of iodotrimethylsilane. Upon completion of addition the reaction mixture was warmed to 60° C. where it stirred for 16 hours. Five ml of methanolic 2N hydrochloric acid was added to the reaction mixture. The solution was stirred for 10 minutes, then concentrated under reduced pressure to a residual solid. The solid was triturated in 25 ml of water. The water/solid mixture was neutralized with aqueous saturated sodium bicarbonate solution. The solid was collected by filtration to give 2-(4-amino-2-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone; m.p. 106°-108° C.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. stirringThe solution was stirred for 10 minutes
  3. concentrationconcentrated under reduced pressure to a residual solid
  4. customThe solid was triturated in 25 ml of water
  5. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-3ce45752126b4e3d81325025a5985e72
Source dataset
uspto-grants-1985_11
Patent number
US04552585

Reaction notes

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