Ethanol → HCID 12878956, compound

HRID 444390Notes

Reaction equation

HRID 444390 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[Cl:9][C:10]1[CH:23]=[CH:22][C:13]([CH:14]=[C:15]([C:19]([O-:21])=O)[C:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.[CH2:24](O)[CH3:25]>Cl.N1C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH:14]2[CH:15]([C:16]([O:18][CH2:24][CH3:25])=[O:17])[C:19](=[O:21])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 87132-AminothiophenolHCID 23463634HCID 23463634, compound

Product 1

HCID 12878956HCID 12878956, compound

Reagents, catalysts & solvents 1

HCID 10176127Pyridinium chlorideCatalyst

Procedure

A mixture of 32 g of o-aminothiophenol, 70.7 g of p-chlorobenzalmalonate and 1.4 g of pyridine hydrochloride was heated at about 180° C. until no further ethanol was distilled out (for about 4 hours). After allowing the reaction mixture to cool, a mixture of benzene-petroleum ether was added to the reaction mixture which was then thoroughly stirred and filtered. The resulting filter cake was recrystallized from chloroform-petroleum ether to obtain 54.5 g of 2-(p-chlorophenyl)-2,3-dihydro-3-ethoxycarbonyl-1,5-benzothiazepin-4(5H)-one as colorless needles having a melting point of 206° C.

Workup

  1. distillationwas distilled out (for about 4 hours)
  2. temperatureto cool
  3. additiona mixture of benzene-petroleum ether
  4. additionwas added to the reaction mixture which
  5. filtrationfiltered
  6. filtrationThe resulting filter cake
  7. customwas recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-76aa82021c8d4430905b1e656bb666a1
Source dataset
uspto-grants-1981_04
Patent number
US04264497

Reaction notes

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