m-Chloroperbenzoic acid → HCID 22478983, compound

HRID 2090231Notes

Reaction equation

HRID 2090231 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:13]=[C:12]1[CH2:24][CH2:25][CH2:26][CH3:27])([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:34].S(=O)(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:16]([O-:34])=[CH:15][C:14]=2[N:13]=[C:12]1[CH2:24][CH2:25][CH2:26][CH3:27])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 516919Sodium BisulfateHCID 22344433HCID 22344433, compound

Product 1

HCID 22478983HCID 22478983, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

The product from step (iv) (0.9 g) was dissolved in DCM (25 mL) and cooled to 5° C. 3-Chloroperoxybenzoic acid (0.203 g) was added and the reaction was allowed to warm to rt. The reaction mixture was stirred for 2 h, more 3-chloroperoxybenzoic acid (0.30 g) was added and the reaction mixture stirred for a further 2 h. The reaction mixture was poured into saturated sodium bisulfate solution, extracted with DCM, dried, filtered and evaporated to give the subtitle (0.9 g).

Workup

  1. temperatureto warm to rt
  2. stirringthe reaction mixture stirred for a further 2 h
  3. extractionextracted with DCM
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give the subtitle (0.9 g)

Sources & evidence

ORD record
ord-02f2366137084460921b5ce08ca64df8
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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