Methanol → 6-tert-Butyl-7-mercapto-1,4-dihydro-quinoxaline-2,3-dione

HRID 1859573Notes

Reaction equation

HRID 1859573 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[S:15]C#N)[NH:11][C:10](=[O:18])[C:9](=[O:19])[NH:8]2)([CH3:4])([CH3:3])[CH3:2].S.[Na].[BH4-].[Na+].CO>CC(O)=O>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[SH:15])[NH:11][C:10](=[O:18])[C:9](=[O:19])[NH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 225728766-Tert-butyl-7-thiocyanato-1,4-dihydro-quinoxaline-2,3-dioneHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 225727956-tert-Butyl-7-mercapto-1,4-dihydro-quinoxaline-2,3-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared according to General Method 14b using 6-tert-butyl-7-thiocyanato-1,4-dihydro-quinoxaline-2,3-dione (prepared in Example CCC; 1.5 g, 9.1 mmol), sodium hydrogen sulfide (0.51 g, 27 mmol), sodium borohydride (2.1 g, 55 mmol), MeOH (30 mL), H20 (3 mL), and glacial AcOH (5 mL). The crude product was used without purification. MS(APCI): 251 (M+H).

Workup

  1. customThe crude product was used without purification

Sources & evidence

ORD record
ord-8b65c9344574478c9886aa6dd1eaf533
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

Loading…