Dichloromethane → HCID 15956321, compound

HRID 724944Notes

Reaction equation

HRID 724944 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:28])[C:7](=[O:27])[C:8]3[CH:18]=[C:17](/C=C\C4C=CC=CC=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.Cl[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([O:38]O)=O)[CH:31]=1.Cl[CH2:41]Cl>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:28])[C:7](=[O:27])[C:8]3[CH:18]=[C:17]([C:36]4([C:32]5[CH:31]=[CH:30][CH:35]=[CH:34][CH:33]=5)[CH2:41][O:38]4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 86751840HCID 86751840, compound

Product 1

HCID 15956321HCID 15956321, compoundYield 21%

Procedure

2-Chloro-5,11-dihydro-11-ethyl-5-methyl-8-(cis-2-phenylethen-1-yl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (prepared by procedures analogous to those described in Example 43) (51 mg, 0.13 mmol) was dissolved in 3 mL of dichloromethane and treated with m-chloroperbenzoic acid (50%, 45 mg, 0.13 mmol) at room temperature. Solid Ca(OH)2 was added, and the reaction mixture was filtered and concentrated. Purification by flash chromatography (elution with ethyl acetate-hexanes) and recrystallization (diethyl ether-hexanes) afforded the title compound (11 mg, 21%), m.p. 105°-107° C.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. customPurification
  4. washby flash chromatography (elution with ethyl acetate-hexanes) and recrystallization (diethyl ether-hexanes)

Sources & evidence

ORD record
ord-49a460a229f9405586654af836cbfd6e
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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