Water → HCID 86593318, compound

HRID 2223997Notes

Reaction equation

HRID 2223997 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]3[S:12][C:13]4[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:14]=4[N:15]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:21][I:22].O>CS(C)=O>[I-:22].[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]3[S:12][C:13]4[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:14]=4[N:15]=3)[CH:8]=[CH:7][C:5]=2[N+:6]=1[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 179535086-Methyl[2,6'-bi-1,3-benzothiazol]-2'-amine

Product 1

HCID 86593318HCID 86593318, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

The 2-aminobenzothiazole 2 (0.3 g, 1.0 mmol) was dissolved in DMSO (2 ml). Methyl iodide (0.25 ml, 2.0 mmol) was added and the mixture was stirred at 110° C. for 17 hours. The mixture was cooled and poured into water. The precipitate formed was collected by filtration and washed with water to give the product as a yellow solid (0.38 g, 86%). Mp 267-269° C.; 1H NMR (DMSO): δ 2.47 (3H, s, Ar—CH3), 3.74 (3H, s, N—CH3), 7.38 (1H, d, J=8.4, ArH), 7.79 (1H, d, J=8.4, ArH), 7.93 (1H, d, J=8.4, ArH), 7.95 (1H, s, ArH), 8.22 (1H, d, J=8.4, ArH), 8.75 (1H, s, ArH), 10.19 (2H, s, NH2); 13C NMR (DMSO): δ 21.14, 32.39, 113.9, 122.0, 122.2, 122.4, 122.7, 126.6, 128.3, 129.8, 134.7, 135.6, 140.9, 151.6, 164.7, 168.9; HR-FAB-MS m/z Found: 312.0638 C16H14N3S2 (M+): requires M, 312.0629.

Workup

  1. temperatureThe mixture was cooled
  2. customThe precipitate formed
  3. filtrationwas collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-3b1463f204cd41e09ae76722fd162839
Source dataset
uspto-grants-2008_05
Patent number
US07378240B2

Reaction notes

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