4-Toluenesulfonyl chloride → Methyl (1,3-benzothiazol-2-yl)acetate

HRID 2099013Notes

Reaction equation

HRID 2099013 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11](=[O:29])[O:12][C:13]2C(C=1)=CC=C(N1CCN(CCO)CC1)C=2.C(N(C(C)C)CC)(C)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>ClCCl.CN(C)C1C=CN=CC=1>[CH3:13][O:12][C:11](=[O:29])[CH2:10][C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86599839HCID 86599839, compound

Product 1

HCID 358756Methyl (1,3-benzothiazol-2-yl)acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

10 mg (0.025 mmol) 3-benzothiazol-2-yl-7-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-chromen-2-one are dissolved in 3 mL dichloromethane with 2.5 mg (0.8 eq.) 4-dimethylaminopyridine and 0.013 mL (3 eq.) diisopropylethylamine, and cooled to 0° C. 5.7 mg (1.2 eq.) tosyl chloride are added and the reaction mixture stirred for one hour before being allowed to reach room temperature. After an additional two hours stirring, the reaction mixture is evaporated, the residue taken up in tetrahydrofurane and treated with 0.2 mL tetrabutylammonium fluoride (1M in THF). After stirring for 30 minutes, the solution is evaporated and the desired product obtained as a yellow powder.

Workup

  1. customto reach room temperature
  2. stirringAfter an additional two hours stirring
  3. customthe reaction mixture is evaporated
  4. additiontreated with 0.2 mL tetrabutylammonium fluoride (1M in THF)
  5. stirringAfter stirring for 30 minutes
  6. customthe solution is evaporated

Sources & evidence

ORD record
ord-f305d20863e0457e9526e40b8db01f2a
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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