HCID 70154633, compound → HCID 53914541, compound

HRID 279245Notes

Reaction equation

HRID 279245 reaction equation
BrC1C=C2CCC3C=C(Cl)C=CC=3C([N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[C@@H:20]([C:31]([N:33]4[CH2:38][CH2:37][CH:36]([CH2:39][CH2:40][CH2:41][N:42]5[CH:46]=[CH:45][N:44]=[CH:43]5)[CH2:35][CH2:34]4)=[O:32])[CH2:19]3)C2=NC=1>ClCCl>[N:42]1([CH2:41][CH2:40][CH2:39][CH:36]2[CH2:37][CH2:38][N:33]([C:31]([C@H:20]3[CH2:19][NH:18][CH2:23][CH2:22][NH:21]3)=[O:32])[CH2:34][CH2:35]2)[CH:46]=[CH:45][N:44]=[CH:43]1

Participants

3

Reactant 1

HCID 70154633HCID 70154633, compound

Product 1

HCID 53914541HCID 53914541, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-peroxybenzoic acid (25 g, 102.59 mmol, 2.5 eq.) in anhydrous dichloromethane (250 mL) was added dropwise over a period of one hour to a stirred solution of 8-chloro-4-aza-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one 1 (10 g, 41.04 mmol, 1.0 eq.) in anhydrous dichloromethane (100 mL) at 0° C. under a nitrogen atmosphere. The solution was slowly (3 h) warmed to room temperature and stirred for another 12 h. The solution was extracted with 1 M aqueous sodium hydroxide solution (5×100 mL), washed with brine (2×100 mL), dried over Na2SO4, filtered, and concentrated under house vacuum at 30° C. to give 2 as a canary-yellow solid. The title compound 2 was used directly without further attempts at purification.

Workup

  1. custom(3 h)
  2. extractionThe solution was extracted with 1 M aqueous sodium hydroxide solution (5×100 mL)
  3. washwashed with brine (2×100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under house vacuum at 30° C.

Sources & evidence

ORD record
ord-45b54a3317f5452da0018265d70bd8df
Source dataset
uspto-grants-2002_03
Patent number
US06362188B1

Reaction notes

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