Sodium Carbonate → 6-(Dimethylamino)hexane-1-thiol

HRID 1289471Notes

Reaction equation

HRID 1289471 reaction equation
CN(C)CCCCCCO.C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1.C([O-])(=S)C.[K+].C([S:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][N:47]([CH3:49])[CH3:48])(C)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.CN(C=O)C.CO.C(N(CC)CC)C>[CH3:48][N:47]([CH3:49])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][SH:40]

Participants

10

Reactant 5

HCID 10340Sodium CarbonateHCID 746236-Dimethylaminohexan-1-olHCID 77773Toluene-p-sulphonic anhydrideHCID 23670855Potassium ethanethioateHCID 131720639HCID 131720639, compound

Product 1

HCID 129471306-(Dimethylamino)hexane-1-thiol

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

6-dimethylaminohexanol was suspended in CH2Cl2 and treated with p-toluenesulphonic anhydride in the presence of triethylamine for 1 hour at 0° C. The reaction mixture was then treated with potassium thioacetate in DMF at 50° C. for a further hour. The resulting compound, AcS(CH2)6NMe2, was treated with sodium carbonate in methanol at room temperature for 20 hours to give 6-(dimethylamino)hexanethiol. This was suspended in dry DMSO at room temperature and sodium hydride was added. The reaction mixture was left stirring for 30 mixtures. 5-bromo-2-thiophenecarboxaldehyde in DMSO was then added and the reaction mixture was warmed to 80° C. for 30 minutes to give the title compound. This is the starting aldehyde used in the preparation of compound 5442.

Sources & evidence

ORD record
ord-5183b8c92d164dbb8edefaf7d53667ce
Source dataset
uspto-grants-1998_05
Patent number
US05750530

Reaction notes

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