2-Aminothiophenol → HCID 86745158, compound

HRID 345300Notes

Reaction equation

HRID 345300 reaction equation
[C:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[CH:14][C:15]([OH:17])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[SH:25]>CN(C)C=O.C(OCC)(=O)C>[C:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]32[CH2:14][C:15](=[O:17])[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[S:25]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 87132-AminothiophenolHCID 54522509HCID 54522509, compound

Product 1

HCID 86745158HCID 86745158, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-phenylmethyl-1-carboxymethylenecyclohexane (3.0 g) and 2-aminothiophenol (5.0 g) in N,N-dimethylformamide (3 ml) was refluxed for 20 hours under nitrogen atmosphere. The mixture was cooled to 0° C. and diluted with ethyl acetate (30 ml) and the mixture was washed with 1N hydrochloric acid (30 ml), water (30 ml), a saturated aqueous solution of sodium bicarbonate (30 ml) and brine (30 ml). The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether to give 2'-phenylmethyl-4,5-dihydro-4-oxospiro[1,5-benzothiazepine-2(3H), 1'-cyclohexane] (2.2 g).

Workup

  1. temperaturewas refluxed for 20 hours under nitrogen atmosphere
  2. washthe mixture was washed with 1N hydrochloric acid (30 ml), water (30 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-c9fd4d5907274083b8b791c6e671dd01
Source dataset
uspto-grants-1991_10
Patent number
US05057513

Reaction notes

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