Carbonic acid-guanidine (1:1) → HCID 13225504, compound

HRID 1979551Notes

Reaction equation

HRID 1979551 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6](=O)[C:7](=[CH:17]N(C)C)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C(=O)(O)O.[NH2:28][C:29]([NH2:31])=[NH:30].C[O-].[Na+]>CO.C(Cl)Cl>[NH2:30][C:29]1[N:31]=[CH:17][C:7]2[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]3[CH:3]=[C:2]([Cl:1])[CH:23]=[CH:22][C:5]=3[C:6]=2[N:28]=1

Participants

6

Reactant 3

HCID 286947Carbonic acid-guanidine (1:1)2×HCID 10942334Sodium Methoxide2×HCID 53830000HCID 53830000, compound

Product 1

HCID 13225504HCID 13225504, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A stirred suspension of 10 g (0.032 mol) of 8-chloro-3,4-dihydro-4-(dimethylaminomethylene)-1-phenyl-5H-2-benzazepin-5-one and 8.5 g (0.047 mol) of guanidine carbonate in 250 ml of methanol was treated at room temperature, under argon, with 5.1 g (0.094 mol) of sodium methylate in one portion. Methylene chloride (150 ml) was added after 10 min and stirring was continued. The same quantities of sodium methylate and guanidine carbonate were added two more times at 2 hr intervals and stirring was continued overnight. After diluting with 250 ml of methylene chloride, the mixture was washed with water, dried over sodium sulfate and evaporated at reduced pressure. Crystallization of the residue from ethanol gave light tan crystals: mp 209°-210° C. Recrystallization of a sample from methylene chloride/ethyl acetate gave off-white prisms: mp 210°-211° C.

Workup

  1. stirringstirring
  2. washthe mixture was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated at reduced pressure
  5. customCrystallization of the residue from ethanol
  6. customgave light tan crystals
  7. customRecrystallization of a sample from methylene chloride/ethyl acetate
  8. customgave off-white prisms

Sources & evidence

ORD record
ord-286dbd91625942f5a8b06043a1a2608a
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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