Water → 5-(1,1-Dimethylethyl)-7-iodo-1,2-benzisoxazole

HRID 263038Notes

Reaction equation

HRID 263038 reaction equation
[CH3:1][C:2]([C:5]1[CH:13]=[C:9]([CH:10]=[N:11]O)[C:8]([OH:14])=[C:7]([I:15])[CH:6]=1)([CH3:4])[CH3:3].ClC(Cl)(Cl)C(N=C=O)=O.C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1>[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([I:15])[C:8]2[O:14][N:11]=[CH:10][C:9]=2[CH:13]=1)([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 76400Trichloroacetyl isocyanateHCID 1363987985-(1,1-Dimethylethyl)-3-iodosalicylaldoxime

Product 1

HCID 130475665-(1,1-Dimethylethyl)-7-iodo-1,2-benzisoxazoleYield 46.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3.19 g of 5-(1,1-dimethylethyl)-3-iodosalicylaldoxime in 10 ml of tetrahydrofuran is added 2.0 g of trichloroacetylisocyanate in tetrahydrofuran (5 ml) at room temperature followed by addition of 1.52 g of potassium carbonate. The mixture is stirred for an additional 20 minutes before it is poured into 400 ml of water. The precipitate so obtained is crystallized from methanol to afford 1.4 g (46.5%) of 5-(1,1-dimethylethyl)-7-iodo-1,2-benzisoxazole, m.p. 106°-109° C.

Workup

  1. customThe precipitate so obtained
  2. customis crystallized from methanol

Sources & evidence

ORD record
ord-4ef0f1efa6db46ca83aaf7911f08e45f
Source dataset
uspto-grants-1979_05
Patent number
US04156005

Reaction notes

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