Hydrochloric Acid → HCID 18001022, compound

HRID 478365Notes

Reaction equation

HRID 478365 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-6c89c21c07124efebeb455167b072d87
Source dataset
uspto-grants-2003_11
Patent number
US06642223B2

Reaction notes

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