Methanesulfonyl chloride → HCID 86680990, compound

HRID 1847955Notes

Reaction equation

HRID 1847955 reaction equation
[Br:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.CCN(C(C)C)C(C)C.C(O)CO.O.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH3:27][S:28]([O:12][CH2:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([Br:1])[S:3][C:4]=2[CH:10]=1)(=[O:30])=[O:29]

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 20437942Ethylene glycol waterHCID 57527160HCID 57527160, compound

Product 1

HCID 86680990HCID 86680990, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-bromobenzo[d]thiazol-6-yl)methanol (205 mg, 0.83 mmol) from Step 2 of this Example and DIEA (118 mg, 0.92 mmol) in CH2Cl2 (20 mL) cooled in an ethylene glycol-water (4:1, v/v) dry ice bath was added methanesulfonyl chloride (105 mg, 0.92 mmol) slowly. The reaction solution was warmed to rt and stirred at rt for 1 h. The resulting mixture was quenched with 20 mL of water. The separated aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure to give (2-bromobenzo[d]thiazol-6-yl)methyl methanesulfonate as a light yellow solid (267 mg, 100%). LCMS (ESI) m/z 322, 324 (M+H)+.

Workup

  1. customThe resulting mixture was quenched with 20 mL of water
  2. extractionThe separated aqueous layer was extracted with CH2Cl2 (3×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3204686031fc43e5b0d305e44a6ad370
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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