Sodium hydrosulfide hydrate → HCID 178528001, compound

HRID 849975Notes

Reaction equation

HRID 849975 reaction equation
C([S:5]([C:8]1[C:12]([CH:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[N:11][S:10][N:9]=1)(=O)=O)CCC.O.[SH-].[Na+]>CN(C=O)C>[SH:5][C:8]1[C:12]([C@H:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[N:11][S:10][N:9]=1

Participants

4

Reactant 2

HCID 16211346Sodium hydrosulfide hydrateHCID 217085323-(3-Butylsulfonyl-1,2,5-thiadiazol-4-yl)-1-azabicyclo[2.2.2]octane

Product 1

HCID 178528001HCID 178528001, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of (3S) 3-(3-butylsulfonyl-1,2,5-thiadiazol-4-yl)-1-azabicyclo[2.2.2]octane (Chirality, 1997, in press.) (1.90 g, 6.0 mmol) in dry DMF (15 ml) was added sodium hydrosulfide monohydrate (1.67 g, 18.0 mmol) and the mixture was stirred at 95° C. for 3 h. The reaction mixture was concentrated in vacuo, added ice water and made less basic with 4 N hydrochloride acid. The precipitate was isolated by filtration to give 1.05 g (77%) of (3S)3-(3-mercapto-1,2,5-thiadiazol-4-yl)-1-azabicyclo[2.2.2]octane.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionadded ice water
  3. customThe precipitate was isolated by filtration

Sources & evidence

ORD record
ord-5d8d0dfdf6a447f289e5bec7b21b06b1
Source dataset
uspto-grants-2000_01
Patent number
US06015813

Reaction notes

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