2-Aminothiophenol → HCID 12878966, compound

HRID 444392Notes

Reaction equation

HRID 444392 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[CH3:9][O:10][C:11]1[CH:26]=[CH:25][C:14]([CH:15]=[C:16]([C:22]([O-])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=1.Cl.C(N(CC)CC)C>C(O)C>[CH2:20]([O:19][C:17]([CH:16]1[C:22](=[O:23])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][CH:15]1[C:14]1[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:26][CH:25]=1)=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 11130Triethylamine hydrochlorideHCID 86737707HCID 86737707, compound

Product 1

HCID 12878966HCID 12878966, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 32 g of o-aminothiophenol, 69.6 g of ethyl p-methoxybenzalmalonate and 1.6 g of triethylamine hydrochloride was heated at about 180° C. until no further ethanol was distilled out (for about 4 hours). The resulting mixture was then worked up in the same manner as described in Reference Example 2 (a) and the crystals thus obtained were recrystallized from chloroform-petroleum ether to obtain 25 g of 2,3-dihydro-3-ethoxycarbonyl-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one as colorless needles having a melting point of 192° C.

Workup

  1. distillationwas distilled out (for about 4 hours)
  2. customthe crystals thus obtained
  3. customwere recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-3a6c47db368f469694ed4994ce6f1e1b
Source dataset
uspto-grants-1981_04
Patent number
US04264497

Reaction notes

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