Methanol → 4-(6-tert-Butyl-5-mercapto-2,3-dihydro-indole-1-sulfonyl)-benzonitrile

HRID 1859554Notes

Reaction equation

HRID 1859554 reaction equation
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][N:11]2[S:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:7][C:6]=1[S:25]C#N)([CH3:4])([CH3:3])[CH3:2].S.[Na].[BH4-].[Na+].CO>CC(O)=O.O>[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][N:11]2[S:14]([C:17]2[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=2)(=[O:15])=[O:16])=[CH:7][C:6]=1[SH:25])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 225730724-(6-tert-Butyl-5-thiocyanato-2,3-dihydro-indole-1-sulfonyl)-benzonitrileHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 225728314-(6-tert-Butyl-5-mercapto-2,3-dihydro-indole-1-sulfonyl)-benzonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The title compound was prepared according to the General Method 14b using 4-(6-tert-butyl-5-thiocyanato-2,3-dihydro-indole-1-sulfonyl)-benzonitrile (prepared in Example MM; 6.0 g, 15 mmol), sodium hydrogen sulfide (2.53 g, 45.3 mmol), sodium borohydride (3.43 g, 90.7 mmol), MeOH (10 mL), water (5 mL), and AcOH (5 mL). The crude product was used further without any purification.

Workup

  1. customThe crude product was used further without any purification

Sources & evidence

ORD record
ord-672e2232cea54aab88fb8df72f87cd75
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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