Tetrahydrofuran → 4-Benzyloxy-1,2-benzisothiazole

HRID 1449119Notes

Reaction equation

HRID 1449119 reaction equation
N[C:2]1[C:10]2[S:9][N:8]=[CH:7][C:6]=2[C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].O1CCCC1.C([O-])(=O)C.[Na+]>Cl.O>[CH2:12]([O:11][C:5]1[C:6]2[CH:7]=[N:8][S:9][C:10]=2[CH:2]=[CH:3][CH:4]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517045Sodium Acetate2×HCID 203499357-Amino-4-benzyloxy-1,2-benzisothiazoleHCID 23668193Sodium Nitrite

Product 1

HCID 203499384-Benzyloxy-1,2-benzisothiazoleYield 60%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

54 g of 7-amino-4-benzyloxy-1,2-benzisothiazole are suspended in 400 ml of half-concentrated hydrochloric acid and diazotized at from 0° to 5° C. with a solution of 16 g of sodium nitrite in 60 ml of water. 500 ml of tetrahydrofuran, 400 ml of a saturated sodium acetate solution and 120 g of sodium acetate are then added and the mixture is allowed to warm up to room temperature. The two-phase reaction medium is then repeatedly extracted with methylene chloride. The combined extracts are dried over magnesium sulfate and then free from solvent under reduced pressure. The crude product is fractionated, giving 30 g (60% of theory) of 4-benzyloxy-1,2-benzisothiazole of melting point 47°-49° C. (boiling point 165° C./0.4 mm Hg).

Workup

  1. customThe two-phase reaction medium
  2. extractionis then repeatedly extracted with methylene chloride
  3. dry with materialThe combined extracts are dried over magnesium sulfate

Sources & evidence

ORD record
ord-88134e4506c449319343217d8576885c
Source dataset
uspto-grants-1980_02
Patent number
US04189433

Reaction notes

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