Carbonic acid-guanidine (1:1) → HCID 13225505, compound

HRID 464514Notes

Reaction equation

HRID 464514 reaction equation
C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].C[O-].[Na+].[Cl:12][C:13]1[CH:35]=[CH:34][C:16]2[C:17](=O)[C:18](=[CH:29]N(C)C)[CH2:19][N:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C:15]=2[CH:14]=1>CO.O>[NH2:7][C:6]1[N:8]=[CH:29][C:18]2[CH2:19][N:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C:15]3[CH:14]=[C:13]([Cl:12])[CH:35]=[CH:34][C:16]=3[C:17]=2[N:5]=1

Participants

6

Reactant 3

HCID 286947Carbonic acid-guanidine (1:1)HCID 10942334Sodium MethoxideHCID 536569248-Chloro-1-(2-chlorophenyl)-4-dimethylaminomethylidene-3,4-dihydro-2-benzazepin-5-one

Product 1

HCID 13225505HCID 13225505, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

In two equal portions 14.4 g (80 mmole) of guanidine carbonate and 20 ml (82 mmole) of 4.12M methanol solution of sodium methoxide was added over 90 min to a solution of 3.6 g (10 mmole) of 8-chloro-1-(2-chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one in 100 ml of methanol. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a yellow oil. Crystallization of the oil with methylene chloride gave a white solid, mp 240°-241° C. Recrystallization from a mixture of ether and methylene chloride gave colorless needles, mp 240°-241° C.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated at reduced pressure
  4. customto give a yellow oil
  5. customCrystallization of the oil with methylene chloride
  6. customgave a white solid, mp 240°-241° C
  7. customRecrystallization
  8. additionfrom a mixture of ether and methylene chloride
  9. customgave colorless needles, mp 240°-241° C.

Sources & evidence

ORD record
ord-1cc2ae7703fa408ca80593b9e1534f5e
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

Loading…