Water → HCID 45077053, compound

HRID 1847974Notes

Reaction equation

HRID 1847974 reaction equation
[H-].[Na+].[SH:3][C:4]1[S:5][C:6]2[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][C:7]=2[N:8]=1.I[CH3:16].O>CN(C=O)C>[CH3:16][S:3][C:4]1[S:5][C:6]2[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][C:7]=2[N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1785095042-Sulfanylidene-2,3-dihydro-1,3-benzothiazole-6-carbonitrile

Product 1

HCID 45077053HCID 45077053, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 1.92 g, 48 mmol) was suspended in DMF (60 mL) at 0° C. and 2-mercaptobenzo[d]thiazole-6-carbonitrile (5.76 g, 30 mmol) from Step 2 of this Example was added slowly. After gas evolution ceased, iodomethane (8.4 mL, 135 mmol) was added and the reaction mixture was stirred at rt overnight. To the reaction mixture was added 300 mL of water and the precipitate was collected by filtration to give 2-(methylthio)benzo[d]thiazole-6-carbonitrile as a light yellow solid (5.47 g, 89%). 1H NMR (300 MHz, CDCl3) δ 8.08 (d, J=1.1 Hz, 1H), 7.91 (d, J=8.3 Hz, 1H), 7.67 (dd, J=1.5, 8.5 Hz, 1H), 2.83 (s, 3H).

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4804364cbd2d4f12b0fae56a1d255821
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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