Acetamidine monohydrochloride → HCID 13271778, compound

HRID 2295974Notes

Reaction equation

HRID 2295974 reaction equation
C[O-].[Na+].C([O:8][C:9]([CH:11]1[C:17]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])=[N:14][CH:13]=[CH:12]1)=O)CCC.C(OC(C1C2C=CC(Cl)=CC=2C(C2C=CC=CC=2F)=NCC=1)=O)CCC.Cl.[C:57]([NH2:60])(=[NH:59])[CH3:58]>C(O)C.O.CO>[Cl:22][C:20]1[CH:19]=[CH:18][C:17]2[CH:11]3[C:9](=[O:8])[NH:60][C:57]([CH3:58])=[N:59][CH:12]3[CH2:13][N:14]=[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:16]=2[CH:21]=1

Participants

8

Reactant 4

HCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 53653079HCID 53653079, compoundHCID 54333506HCID 54333506, compound

Product 1

HCID 13271778HCID 13271778, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In one portion 14.0 mL of a 4.34 M methanol solution of sodium methoxide was added to a solution of 14.0 g (37.7 mmol) of a mixture of 8-chloro-1-(2-fluorophenyl)-5H-2-benzazepine-5-carboxylic acid butyl ester and 8-chloro-1-(2-fluorophenyl)-3H-2-benzazepine-5-carboxylic acid butyl ester and 7.0 g (74 mmol) of acetamidine hydrochloride in 250 mL of ethanol. The mixture was refluxed for 17 hr, cooled and poured into 1 L of water. The resulting precipitate was collected by filtration and washed with ether to yield an off-white solid, mp 150°-165°.

Workup

  1. temperatureThe mixture was refluxed for 17 hr
  2. temperaturecooled
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with ether
  5. customto yield an off-white solid, mp 150°-165°

Sources & evidence

ORD record
ord-cd58c9fc78ff41d386b19425f09f60ea
Source dataset
uspto-grants-1984_01
Patent number
US04427589

Reaction notes

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