Hydrochloric Acid → HCID 14986574, compound

HRID 1613132Notes

Reaction equation

HRID 1613132 reaction equation
[C:1]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[NH:12][C:11]=2[CH:21]=1)([O:3][CH2:4][CH3:5])=[O:2].[Br:22][CH:23]([CH3:27])[C:24](Cl)=[O:25].Cl>C1(C)C=CC=CC=1>[C:1]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[N:12]([C:24](=[O:25])[CH:23]([Br:22])[CH3:27])[C:11]=2[CH:21]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 979802-Bromopropanoyl chlorideHCID 2834073HCID 2834073, compound

Product 1

HCID 14986574HCID 14986574, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The starting material can be synthesized as follows. 3-Carbethoxyamino-10,11-dihydro-5H-dibenz[b,f]azepine (28.2 g, 0.1 moles) is mixed with 300 ml toluene and 20 g (0.11 moles) of 2-bromopropionyl chloride and stirred for 4 hours on a boiling water bath, while HCl gas is escaping. The mixture is allowed to cool to room temperature and filtered and the filtrate is evaporated to dryness under reduced pressure. Upon addition of diethyl ether, the residue crystallizes, after temporarily going into solution. The crystalline deposit is filtered off with suction, washed with ether and dried. 3-Carbethoxyamino-5-(α-bromopropionyl)-10,11-dihydro-5H-dibenz[b,f]azepine (39 g) is obtained, which is purified by recrystallization from the 5-fold amount of isopropanol.

Workup

  1. customThe starting material can be synthesized
  2. filtrationfiltered
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. additionUpon addition of diethyl ether
  5. customthe residue crystallizes
  6. filtrationThe crystalline deposit is filtered off with suction
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-1196eeed783840a2a77b027fac694526
Source dataset
uspto-grants-1993_03
Patent number
US05192760

Reaction notes

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