Chlorosuccinimide → HCID 178501059, compound

HRID 1893354Notes

Reaction equation

HRID 1893354 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[O:12][CH:13]=[C:14]([CH3:16])[N:15]=2)[CH2:7][CH2:6]1)=[O:4].[Cl:17]N1C(=O)CCC1=O>CN(C)C=O>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[O:12][C:13]([Cl:17])=[C:14]([CH3:16])[N:15]=2)[CH2:9][CH2:10]1)=[O:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178501060HCID 178501060, compound

Product 1

HCID 178501059HCID 178501059, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of trans-4-(4-methyl-oxazol-2-yl)-cyclohexanecarboxylic acid methyl ester (277 mg, 1.24 mmol) and N-chlorosuccinimide (182 mg, 1.36 mmol) in N,N-dimethylformamide (2.5 ml) was stirred for 6 h at room temperature. The reaction mixture was partitioned between tert-butyl methyl ether (25 ml) and 0.1 M aqueous sodium hydroxide solution (25 ml). The layers were separated. The aqueous layer was extracted with one 25-ml portion of tert-butyl methyl ether. The combined organic layers were washed with three 25-ml portions of water, dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude title compound (285 mg, 89%) as light yellow solid, which was used in the next step without further purification. MS m/e: 258 ([M+H]+)

Workup

  1. customThe reaction mixture was partitioned between tert-butyl methyl ether (25 ml) and 0.1 M aqueous sodium hydroxide solution (25 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with one 25-ml portion of tert-butyl methyl ether
  4. washThe combined organic layers were washed with three 25-ml portions of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-08fe932b58f34c7a83c9ef7b04a07b1b
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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