Lithium Bromide → HCID 70403832, compound

HRID 580420Notes

Reaction equation

HRID 580420 reaction equation
COC([C:5]1([CH2:25][CH:26]=[CH2:27])[CH:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:10][C:9]2[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=2[NH:7][C:6]1=[O:24])=O.[Br-].[Li+]>CN(C)C=O.O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C@H:11]2[CH2:10][C:9]3[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=3[NH:7][C:6](=[O:24])[C@H:5]2[CH2:25][CH:26]=[CH2:27])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 82050Lithium BromideHCID 15612169HCID 15612169, compound

Product 1

HCID 70403832HCID 70403832, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-3-(2-propenyl)-2H-1-benzazepin-2-one (4.56 g, 12.48 mmol), lithium bromide (6.18 g, 71.13 mmol) and α-aminothiophenol (3.12 g, 24.96 mmol) in 38 ml of dry dimethylformamide was heated to 137° C. (oil bath temperature) under argon for 51/2 hours. The reaction mixture was cooled to room temperature and diluted with water (250 ml total volume). The precipitate was collected by filtration, rinsed with 1M hydrochloric acid, saturated aqueous potassium carbonate solution, water, and dried in vacuo with phosphorous pentoxide to give 3.5 g of a white solid. Recrystallization from methanol (3 crops) yielded 3.03 g of white needles, melting point 169°-171° C.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washrinsed with 1M hydrochloric acid, saturated aqueous potassium carbonate solution, water
  3. dry with materialdried in vacuo with phosphorous pentoxide

Sources & evidence

ORD record
ord-0db7dd873a284c959cbc6eb2980d58b6
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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