Carbon Dioxide → 1,3-Benzothiazol-6-ylmethyl methanesulfonate

HRID 607577Notes

Reaction equation

HRID 607577 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([CH2:10][OH:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C(N(CC)C(C)C)(C)C.C(=O)=O.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl.C(O)CO.O>[CH3:24][S:25]([O:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]2[N:3]=[CH:2][S:1][C:5]=2[CH:6]=1)(=[O:27])=[O:26]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178603856-(Hydroxymethyl)benzothiazole

Product 1

HCID 592162921,3-Benzothiazol-6-ylmethyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 20437942Ethylene glycol waterSolvent

Procedure

1,3-benzothiazol-6-ylmethanol (1.56 g, 0.00944 mol) and N,N-diisopropylethylamine (2.47 mL, 0.0142 mol) were stirred in methylene chloride (16 mL). The reaction mixture was cooled in an ethylene glycol/water (4/1)/dry ice bath. To the solution was added dropwise a solution of methanesulfonyl chloride (1.10 mL, 0.0142 mol) in DCM (2 mL). After 30 min the reaction mixture was quenched by adding water, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the desired product which was directly used in the next step without purification. LCMC: (M+H)+=244.2.

Workup

  1. customAfter 30 min the reaction mixture was quenched
  2. additionby adding water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0755246e68c84c1ab3edcc21107a7b35
Source dataset
uspto-grants-2011_03
Patent number
US07915408B2

Reaction notes

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