Diethyl Ether → HCID 178482864, compound

HRID 1199450Notes

Reaction equation

HRID 1199450 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([S:9][C:10]3[CH:15]=[C:14]([N:16]([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=3[N:19]([CH3:21])[CH3:20])=[N:8][C:4]=2[CH:3]=1.ClC1C=CC=C(C(OO)=[O:32])C=1.CCOCC>C(OCC)(=O)C>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([S:9]([C:10]3[CH:15]=[C:14]([N:16]([CH3:17])[CH3:18])[CH:13]=[CH:12][C:11]=3[N:19]([CH3:21])[CH3:20])=[O:32])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 178482863HCID 178482863, compound

Product 1

HCID 178482864HCID 178482864, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The product of step (a) above (550 mg) was dissolved in ethyl acetate (20 ml) and cooled to -10°. A solution of m-chloroperbenzoic acid (320 mg of 85%) in ethyl acetate (5 ml) was cooled to 0° and added to the above solution. After stirring at below 0° for 3 hours the solution was washed with sodium bicarbonate solution, sodium metabisulphite solution, water and brine, and then dried and concentrated in vacuo. The residue was flash chromatographed to produce a yellow gum. Trituration with ether and petroleum ether produced the title compound as a pale yellow solid (125 mg), mp 161°-3°.

Workup

  1. temperaturecooled to -10°
  2. additionadded to the above solution
  3. washwas washed with sodium bicarbonate solution, sodium metabisulphite solution, water and brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customchromatographed
  7. customto produce a yellow gum

Sources & evidence

ORD record
ord-4b5ff226932d4395b67c38be088bd6e4
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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