Ammonia → HCID 53954039, compound

HRID 1729625Notes

Reaction equation

HRID 1729625 reaction equation
[CH2:1]([Li])CCC.[CH3:6][O:7][C:8]([CH:10]1[C:16](=[O:17])[C:15]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:14]=2[NH:13][C:12](=[O:23])[CH2:11]1)=[O:9].CI.[Cl-].[NH4+].N>CCCCCC.C(OCC)C>[CH3:6][O:7][C:8]([CH:10]1[C:16](=[O:17])[C:15]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:14]=2[N:13]([CH3:1])[C:12](=[O:23])[CH2:11]1)=[O:9]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 54308116HCID 54308116, compoundHCID 178418339Butyllithium

Product 1

HCID 53954039HCID 53954039, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To the mixture, prepared from the dropwise addition of 131 ml of 1.6 molar n-butyl lithium in hexane to 600 ml of liquid amonia while vigorously stirring under an artificial atmosphere of nitrogen for 40 minutes at -76°, 26.7 g of 8-chloro-2,3,4,5-tetrahydro-1-benzazepine-2,5-dione-4-carboxylic acid methyl ester are added all at once and the solution obtained stirred for 1 hour. Thereupon 14.2 g of methyl iodide are added dropwise and the mixture stirred at -35° for 3 hours. It is conbined with 24 g of ammonium chloride and 600 ml of diethyl ether and the ammonia is allowed to evaporate over night at room temperature. 500 ml of water are added to the mixture, its pH adjusted to 6-7 with 6N hydrochloric acid, the organic phase separated and the aqueous layer extracted with diethyl ether. The combined organic solutions are washed with water, dried, filtered, evaporated and the residue recrystallized from diethyl ether, to yield the 8-chloro-1-methyl-2,3,4,5-tetrahydro-1-benzazepine-2,5-dione-4-carboxylic acid methyl ester melting at 134°-136°.

Workup

  1. customobtained
  2. stirringstirred for 1 hour
  3. stirringthe mixture stirred at -35° for 3 hours
  4. customto evaporate over night at room temperature
  5. addition500 ml of water are added to the mixture, its pH
  6. customthe organic phase separated
  7. extractionthe aqueous layer extracted with diethyl ether
  8. washThe combined organic solutions are washed with water
  9. customdried
  10. filtrationfiltered
  11. customevaporated
  12. customthe residue recrystallized from diethyl ether

Sources & evidence

ORD record
ord-4652ce06225a46d9b46a69a583c1a890
Source dataset
uspto-grants-1976_11
Patent number
US03989689

Reaction notes

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