Water → HCID 178526224, compound

HRID 464547Notes

Reaction equation

HRID 464547 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6](=O)[C:7](=[CH:19]N(C)C)[CH2:8][N+:9]([O-:18])=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1.[NH2:26][C:27]([NH2:29])=[S:28].C[O-].[Na+].O>CO>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]3[N:29]=[C:27]([SH:28])[N:26]=[CH:19][C:7]=3[CH2:8][N+:9]([O-:18])=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2723790ThioureaHCID 10942334Sodium MethoxideHCID 73165729HCID 73165729, compound

Product 1

HCID 178526224HCID 178526224, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 1.5 g (4 mmol) of 8-chloro-1-(2-fluorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one-2-oxide, 1.5 g (20 mmol) of thiourea and 5 ml of a 4M methanol solution of sodium methoxide in 30 ml of methanol was stirred at room temperature for 5 hr. The mixture was poured into water and extracted with ether. The aqueous solution was acidified with acetic acid and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure. The residue was triturated with methylene chloride to give an orange solid. Recrystallization from methylene chloride gave the product as orange crystals, mp 323°-325° C. (dec.).

Workup

  1. extractionextracted with ether
  2. extractionextracted with methylene chloride
  3. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was triturated with methylene chloride
  6. customto give an orange solid
  7. customRecrystallization from methylene chloride

Sources & evidence

ORD record
ord-af16d62349ab44539dcff8695faa5b8b
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

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