Potassium Carbonate → HCID 178527999, compound

HRID 849974Notes

Reaction equation

HRID 849974 reaction equation
C([S:4]([C:7]1[C:11]([CH:12]2[CH:17]3[CH2:18][N:14]([CH2:15][CH2:16]3)[CH2:13]2)=[N:10][S:9][N:8]=1)(=O)=O)CC.C(=O)([O-])[O-].[K+].[K+].O.[SH-].[Na+]>CN(C=O)C>[N:14]12[CH2:18][CH:17]([CH2:16][CH2:15]1)[CH:12]([C:11]1[C:7]([SH:4])=[N:8][S:9][N:10]=1)[CH2:13]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16211346Sodium hydrosulfide hydrate2×HCID 19365779HCID 19365779, compound

Product 1

HCID 178527999HCID 178527999, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Endo (-) 3-(3-(3-propylsulfonyl-1,2,5-thiadiazol-4-yl)-1-azabicyclo[2.2.1]heptane (W094/20496) (1.5 g, 5.2 mmol) and potassium carbonate (1.4 g, 10.4 mmol) in dry DMF(20 ml) was added sodium hydrosulfide monohydrate (1.15 g, 15.6 mmol). The reaction mixture was heated to 70° C. During this period another two portions of sodium hydrosulfide monohydrate was added to complete the reaction. DMF was evaporated and the residue added ice water followed by 4 N hydrochloric acid to pH 8-9. The product was isolated by filtration to give 862 mg (78%) of Endo (β) 4-(1-azabicyclo[2.2.1]hept-3-yl)-1,2,5-thiadiazol-3-thiol.

Workup

  1. customthe reaction
  2. customDMF was evaporated
  3. additionthe residue added ice water
  4. customThe product was isolated by filtration

Sources & evidence

ORD record
ord-9e14233ddaaf44359927d3538c7a300e
Source dataset
uspto-grants-2000_01
Patent number
US06015813

Reaction notes

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