Carbonic acid-guanidine (1:1) → HCID 13225512, compound

HRID 1979576Notes

Reaction equation

HRID 1979576 reaction equation
C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].C[O-].[Na+].[Cl:12][C:13]1[CH:36]=[CH:35][C:16]2[C:17](=O)[C:18](=[CH:30]N(C)C)[CH2:19][N+:20]([O-:29])=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:15]=2[CH:14]=1>CO.O>[NH2:7][C:6]1[N:8]=[CH:30][C:18]2[CH2:19][N+:20]([O-:29])=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:15]3[CH:14]=[C:13]([Cl:12])[CH:36]=[CH:35][C:16]=3[C:17]=2[N:5]=1

Participants

6

Reactant 3

HCID 286947Carbonic acid-guanidine (1:1)HCID 10942334Sodium MethoxideHCID 73165729HCID 73165729, compound

Product 1

HCID 13225512HCID 13225512, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

In two equal portions 28 g (150 mmole) of guanidine carbonate and 38 ml (150 mmole) of a 4.09 M methanol solution of sodium methoxide was added over a 2 hr period to a solution of 7.0 g (20 mmole) of 8-chloro-1-(2-fluorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one-2-oxide in 210 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 red solid. Recrystallization from a mixture of methanol and ethyl acetate gave the product as fine yellow needles, m.p. 320°-323° 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 red solid
  5. customRecrystallization
  6. additionfrom a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-8965d272aaee4bf598ba2401aed76367
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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