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

HRID 23498Notes

Reaction equation

HRID 23498 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.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

7

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 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

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), H2O (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-c1fb75527546481183c8b2513d97bd04
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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