2-Aminothiophenol → HCID 12878961, compound

HRID 444391Notes

Reaction equation

HRID 444391 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[CH3:9][C:10]1[CH:23]=[CH:22][C:13]([CH:14]=[C:15]([C:19]([O-:21])=[O:20])[C:16]([O-:18])=O)=[CH:12][CH:11]=1.Cl.[CH2:25](N(CC)CC)[CH3:26]>C(O)C>[CH2:25]([O:21][C:19]([CH:15]1[C:16](=[O:18])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][CH:14]1[C:13]1[CH:12]=[CH:11][C:10]([CH3:9])=[CH:23][CH:22]=1)=[O:20])[CH3:26]

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 11130Triethylamine hydrochlorideHCID 19425805HCID 19425805, compound

Product 1

HCID 12878961HCID 12878961, compoundYield 979.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 32 g of o-aminothiophenol, 65.6 g of p-methylbenzalmalonate and 1.4 g of triethylamine hydrochloride was heated at about 180° C. until no further ethanol was distilled out (for about 3 hours). The resulting reaction mixture was worked up in the same manner as described in Reference Example 2 (a) and the crystals thus obtained was recrystallized from chloroform-petroleum ether to obtain 34 g of 2,3-dihydro-3-ethoxycarbonyl-2-(p-tolyl)-1,5-benzothiazepin-4(5H)-one as light yellow needles having a melting point of 185° C.

Workup

  1. distillationwas distilled out (for about 3 hours)
  2. customThe resulting reaction mixture
  3. customthe crystals thus obtained
  4. customwas recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-bf5f8af2e2014eadbbaac7be851ad30d
Source dataset
uspto-grants-1981_04
Patent number
US04264497

Reaction notes

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