Methanesulfonyl chloride → HCID 67257981, compound

HRID 1619299Notes

Reaction equation

HRID 1619299 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]([OH:7])=O.CS(Cl)(=O)=O.[NH2:13][C:14]1[CH:23]=[C:22]([Br:24])[CH:21]=[CH:20][C:15]=1[C:16]([NH:18][CH3:19])=[O:17]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:24][C:22]1[CH:21]=[CH:20][C:15]([C:16]([NH:18][CH3:19])=[O:17])=[C:14]([NH:13][C:5](=[O:7])[CH2:4][CH2:3][O:2][CH3:1])[CH:23]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 1344423-Methoxypropionic acidHCID 23158201HCID 23158201, compound

Product 1

HCID 67257981HCID 67257981, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-methoxypropanoic acid (0.25 mL, 2.62 mmol), DMAP (0.64 g, 5.24 mmol) and dry DCM (5 mL) was added methanesulfonyl chloride (0.22 mL, 2.88 mmol) dropwise at 0° C. under nitrogen atmosphere. 2-Amino-4-bromo-N-methylbenzamide (0.3 g, 1.31 mmol) was added after stirring for 1 h, and the temperature was allowed to rise to room temperature slowly. The reaction mixture was quenched with sat. NH4Cl solution after 3 h and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with NaHCO3, dried over Na2SO4, filtered, and evaporated to give 0.39 g of the target compound. MS (ESI): 315, 317 (MH+).

Workup

  1. customto rise to room temperature
  2. customThe reaction mixture was quenched with sat. NH4Cl solution after 3 h
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. washThe combined organic layers were washed with NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-be5ebe60f8b34f2f9f005d6ef0bdf851
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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