Hydrochloric Acid → HCID 13712508, compound

HRID 2352219Notes

Reaction equation

HRID 2352219 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9]1(=O)[CH:18]2[CH:13]([CH2:14][CH:15]=[CH:16][CH2:17]2)[C:12](=[O:19])[CH:11]=[CH:10]1.Cl.C([O-])(O)=O.[Na+]>CO.C(OCC)(=O)C>[OH:19][C:12]1[CH:11]=[C:10]2[C:9]([NH:1][C:2]3[C:3]([S:8]2)=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:18]2[CH2:17][CH:16]=[CH:15][CH2:14][C:13]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 87132-AminothiophenolHCID 226554a,5,8,8a-Tetrahydro-1,4-naphthoquinoneHCID 516892Sodium Bicarbonate

Product 1

HCID 13712508HCID 13712508, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-aminothiophenol (385 mg) in methanol (3 ml) was added to a solution of 4a, 5, 8, 8a-tetrahydro-1,4-naphtoquinone (Ref.: Ber. 62, 2361 (1929)) (500 mg) in methanol (10 ml) and stirred for 1 hour. Then conc. HCl (2 ml) was added and the mixture was stirred for another 2 hours. Ethyl acetate was added to the reaction mixture followed by a solution of NaHCO3. The organic layer was decanted, dried and evaporated to dryness. The resulting oily residue was chromatographed on silica gel (CH2Cl2) to afford the title compound.

Workup

  1. stirringthe mixture was stirred for another 2 hours
  2. customThe organic layer was decanted
  3. customdried
  4. customevaporated to dryness
  5. customThe resulting oily residue was chromatographed on silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-d20f1ca869b94a7484f45b49669a02cc
Source dataset
uspto-grants-1989_10
Patent number
US04876246

Reaction notes

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