Carbonic acid-guanidine (1:1) → HCID 9862708, compound

HRID 1979552Notes

Reaction equation

HRID 1979552 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6](=O)[C:7](=[CH:18]N(C)C)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1.C(=O)(O)O.[NH2:29][C:30]([NH2:32])=[NH:31].C[O-].[Na+]>CO.C(Cl)Cl>[NH2:31][C:30]1[N:32]=[CH:18][C:7]2[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]3[CH:3]=[C:2]([Cl:1])[CH:24]=[CH:23][C:5]=3[C:6]=2[N:29]=1

Participants

6

Reactant 3

HCID 286947Carbonic acid-guanidine (1:1)2×HCID 10942334Sodium Methoxide2×HCID 54487933HCID 54487933, compound

Product 1

HCID 9862708HCID 9862708, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A stirred suspension of 16 g (0.047 mol) of 8-chloro-1-(2-fluorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one and 12.5 g (0.07 mol) of guanidine carbonate in 460 ml of methanol was treated at room temperature, under argon, with 7.5 g (0.14 mol) of sodium methylate in one portion. Methylene chloride (290 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 460 ml of methylene chloride, the mixture was washed with water, dried over sodium sulfate and evaporated at reduced pressure. Recrystallization of the residue from ethanol/methylene chloride solution gave off-white crystals: mp 245°-248° C.

Workup

  1. stirringstirring
  2. washthe mixture was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated at reduced pressure
  5. customRecrystallization of the residue from ethanol/methylene chloride solution
  6. customgave off-white crystals

Sources & evidence

ORD record
ord-b2da1c4a7cc147f9b7ecf91f6f70d9bd
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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