Methanol → HCID 19866724, compound

HRID 1199466Notes

Reaction equation

HRID 1199466 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[N:21]([CH3:22])[C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N:18]=1.CO.ClC1C=CC=C(C(OO)=[O:37])C=1>ClCCl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[N:21]([CH3:22])[C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N:18]=1)=[O:37]

Participants

5

Reactant 3

HCID 887MethanolHCID 70297m-Chloroperbenzoic acidHCID 15059547HCID 15059547, compound

Product 1

HCID 19866724HCID 19866724, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step (d) above (0.99 g) was dissolved in dichloromethane (60 ml) and methanol (5 ml) and cooled to -10°. 85% m-Chloroperbenzoic acid (0.56 g) was added and the whole was slowly warmed to room temperature with stirring. After 2 hours the reaction mixture was washed with metabisulphate solution, then bicarbonate solution and finally with brine, dried over magnesium sulphate and evaporated to dryness in vacuo and the residue was purified by flash chromatography (SiO2 /CH2Cl2 2:3 ethyl acetate) to afford the title compound as a white solid, mp 164°.

Workup

  1. washAfter 2 hours the reaction mixture was washed with metabisulphate solution
  2. dry with materialbicarbonate solution and finally with brine, dried over magnesium sulphate
  3. customevaporated to dryness in vacuo
  4. customthe residue was purified by flash chromatography (SiO2 /CH2Cl2 2:3 ethyl acetate)

Sources & evidence

ORD record
ord-425e3a263cf94be8acab0c0b1739fb8b
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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