Diethyl Ether → HCID 19427682, compound

HRID 1078549Notes

Reaction equation

HRID 1078549 reaction equation
[CH:1]1([N:4]2[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8]([S:15][CH3:16])=[N:7][C:6]3[C:17]([CH3:21])=[CH:18][CH:19]=[N:20][C:5]2=3)[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:30])C=1.CCOCC>C(Cl)Cl>[CH:1]1([N:4]2[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8]([S:15]([CH3:16])=[O:30])=[N:7][C:6]3[C:17]([CH3:21])=[CH:18][CH:19]=[N:20][C:5]2=3)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 19427671HCID 19427671, compound

Product 1

HCID 19427682HCID 19427682, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 11-cyclopropyl-4-methyl-6-methylthio-11H-dipyrido[3,2-b:2',3'-e][1,4]diazepine (0.8 g, 0.0027 mol) in methylene chloride (10 mL) was cooled in an ice water bath. To the resulting clear yellow solution was added m-chloroperbenzoic acid (0.55 g, 0.0027 mol) in one portion and the reaction mixture was stirred at 0° C. for 30 min. A cloudy yellow solution was obtained which was quenched by the addition of Ca(OH)2 (1 g, 0.0135 mol). The reaction mixture was stirred at room temperature for 15 min., filtered through a pad of Celite, and concentrated to obtain a yellow oil. Trituration with ether afforded 0.7 g of the title compound, m.p. 188°-190° C.

Workup

  1. customA cloudy yellow solution was obtained which
  2. stirringThe reaction mixture was stirred at room temperature for 15 min.
  3. filtrationfiltered through a pad of Celite
  4. concentrationconcentrated
  5. customto obtain a yellow oil

Sources & evidence

ORD record
ord-26f8b8bb7ec4449d8c75a16774aef9fc
Source dataset
uspto-grants-1996_08
Patent number
US05550117

Reaction notes

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