Hydrochloric Acid → HCID 18001022, compound

HRID 1249991Notes

Reaction equation

HRID 1249991 reaction equation
CSC.[Cl-].[Al+3].[Cl-].[Cl-].C[O:9][C:10]([CH2:12][CH:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]([C:24](=[O:42])[C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:41])[CH2:33][O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:27][CH:26]=2)[CH2:16][CH2:15][CH2:14]1)=[O:11].Cl>ClCCl>[C:10]([CH2:12][CH:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]([C:24](=[O:42])[C:25]2[CH:26]=[CH:27][C:28]([NH:31][C:32](=[O:41])[CH2:33][O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:29][CH:30]=2)[CH2:16][CH2:15][CH2:14]1)([OH:11])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1068Dimethyl SulfideHCID 6451240Aluminum(III) ChlorideHCID 18001017HCID 18001017, compound

Product 1

HCID 18001022HCID 18001022, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To dimethylsulfide (170 ml) is added dropwise with stirring aluminum chloride (23.6 g) under ice-cooling, and further thereto is added dropwise a solution of 5-methoxycarbonylmethyl-1-[4-(2-phenoxyacetylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (16.76 g) in dichloromethane (150 ml), and the mixture is stirred at room temperature for two hours. The reaction mixture is poured into a mixture of conc. hydrochloric acid and crashed ice, and the mixture is extracted with dichloromethane. The organic layer is washed with water, dried over magnesium sulfate, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=30:1) to give 5-carboxymethyl-1-[4-(2-phenoxyacetylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (13.67 g) as white powder.

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with dichloromethane
  3. washThe organic layer is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-89aa714a02814350a330e38045367cde
Source dataset
uspto-grants-2002_01
Patent number
US06335327B1

Reaction notes

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