Water → HCID 17953516, compound

HRID 2223998Notes

Reaction equation

HRID 2223998 reaction equation
[I-].[NH2:2][C:3]1[S:4][C:5]2[CH:12]=[C:11]([C:13]3[S:14][C:15]4[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:16]=4[N:17]=3)[CH:10]=[CH:9][C:6]=2[N+:7]=1[CH3:8].O.[OH-].[Na+]>CS(C)=O>[NH:2]=[C:3]1[N:7]([CH3:8])[C:6]2[CH:9]=[CH:10][C:11]([C:13]3[S:14][C:15]4[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:12][C:5]=2[S:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86593318HCID 86593318, compound

Product 1

HCID 17953516HCID 17953516, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-amino-3-methyl-6-(6-methyl-benzothiazol-2-yl)-benzothiazolium iodide (0.3 g, 0.68 mmol) was taken up in DMSO (10 ml). Water was added (20 ml) and the mixture was basified to pH 10 with aqueous NaOH (20%). The precipitate was collected by filtration and washed with water to produce 3 as a light yellow solid (0.19 g, 89%). Mp 146-148° C.; 1H NMR (DMSO): 2.45 (3H, s, Ar—CH3), 3.38 (3H, s, N—CH3), 7.16 (1H, d, J=8.4, ArH), 7.33 (1H, d, J=8.4, ArH), 7.87 (1H, s, ArH), 7.90 (1H, s; ArH), 7.93 (1H, d, J=8.4, ArH), 8.16 (1H, s, ArH), 8.55 (1H, s, NH); 13C NMR analysis was not possible due to poor solubility of 4 in available deuterated solvents; HR-FAB-MS m/z Found: 312.0619 C16H14N3S2 (M+H+): requires M, 312.0629.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-d0e881e00cb5403a8f381f6c581d19a6
Source dataset
uspto-grants-2008_05
Patent number
US07378240B2

Reaction notes

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