2-Aminothiophenol → HCID 58548537, compound

HRID 1846778Notes

Reaction equation

HRID 1846778 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[CH3:9][O:10][CH:11]1[CH2:16][CH2:15][CH:14]([C:17](O)=O)[CH2:13][CH2:12]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>C(Cl)Cl>[CH3:9][O:10][CH:11]1[CH2:16][CH2:15][CH:14]([C:17]2[S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 87949Lawesson's reagentHCID 736153Rac-(1r,4r)-4-methoxycyclohexane-1-carboxylic acid

Product 1

HCID 58548537HCID 58548537, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-amino-benzenethiol (796 mg, 6.32 mmol), 4-methoxy-cyclohexanecarboxylic acid (1.0 g, 6.32 mmol) and Lawesson reagent (889 mg, 2.2 mmol) was heated to 160˜190° C. for 1 h. Then the mixture was diluted with DCM (100 ml) and washed with 10% aqueous NaOH solution (2×10 mL), brine, and dried over Na2SO4. The organic layer was concentrated and purified by flash column chromatography to give 2-(4-methoxy-cyclohexyl)-benzothiazole which was used in the next step without further purification.

Workup

  1. temperaturewas heated to 160˜190° C. for 1 h
  2. washwashed with 10% aqueous NaOH solution (2×10 mL), brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic layer was concentrated
  5. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-d9164c3203c04932a4bc3c2a027324b5
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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