Water → 7-Allyloxy-2-methyl-benzothiazole

HRID 366467Notes

Reaction equation

HRID 366467 reaction equation
[OH:1][C:2]1[C:10]2[S:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20].O>CN(C=O)C>[CH2:20]([O:1][C:2]1[C:10]2[S:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH:19]=[CH2:18]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 232893082-Methylbenzo[d]thiazol-7-ol

Product 1

HCID 232893417-Allyloxy-2-methyl-benzothiazoleYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To 7-hydroxy-2-methylbenzothiazole (500 mg, 3.0 mmol) in DMF (3 mL) was added K2CO3 (459 mg, 3.32 mmol) followed by allyl bromide (287 uL, 3.32 mmol). The reaction was heated at about 50° C. for about 4 hours and then poured into water. The aqueous mixture was extracted with EtOAc, the combined organic layers were dried over Na2SO4, and the solvent then removed by rotary evaporation. The resulting oil crystallized on standing to give 7-allyloxy-2-methyl-benzothiazole as yellow crystals (440 mg, 71%); LSIMS m/z 206, m.p. 38-39° C.

Workup

  1. extractionThe aqueous mixture was extracted with EtOAc
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. customthe solvent then removed by rotary evaporation
  4. customThe resulting oil crystallized

Sources & evidence

ORD record
ord-9206c6099e3a436e85cd088984c81279
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Reaction notes

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