Hydrochloric Acid → HCID 13225503, compound

HRID 464170Notes

Reaction equation

HRID 464170 reaction equation
[ClH:1].[C:2]([NH2:5])(=[NH:4])[CH3:3].C[O-].[Na+].[C:9]1([C:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[C:19](=O)[C:18](=[CH:27]N(C)C)[CH2:17][N:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>CO.C(Cl)Cl>[ClH:1].[ClH:1].[CH3:3][C:2]1[N:4]=[CH:27][C:18]2[CH2:17][N:16]=[C:15]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[C:19]=2[N:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 53970306HCID 53970306, compound

Product 1

HCID 13225503HCID 13225503, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

In five equal portions 9.0 g (95 mmole) of acetamidine hydrochloride and 22.5 (0.1 mole) of a 4.46M methanol solution of sodium methoxide was added over 3 hr to a solution of 4.5 g (15 mmole) of 1-phenyl-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one in 180 ml of methanol and 180 ml of methylene chloride. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to give an oil. The oil was dissolved in an excess of 6% methanolic hydrogen chloride and the solvent was removed at reduced pressure to dryness. The residue was crystallized from a mixture of ether and methylene chloride to give a white solid mp 211°-221° C. Recrystallization from a mixture of methanol and ether gave white flakes, mp 217°-227° C.

Workup

  1. washThe methylene chloride solution was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated at reduced pressure
  4. customto give an oil
  5. customthe solvent was removed at reduced pressure to dryness
  6. customThe residue was crystallized from a mixture of ether and methylene chloride

Sources & evidence

ORD record
ord-59bb213a0aa54c468ab548fddfa38590
Source dataset
uspto-grants-1985_10
Patent number
US04546183

Reaction notes

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