Water → 4-Methyl-2,1,3-benzothiadiazole

HRID 723732Notes

Reaction equation

HRID 723732 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[S:10](Cl)(Cl)=O.O>N1C=CC=CC=1>[CH3:9][C:3]1[C:2]2=[N:1][S:10][N:8]=[C:7]2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 175932,3-DiaminotolueneHCID 24386Thionyl Chloride

Product 1

HCID 27812624-Methyl-2,1,3-benzothiadiazoleYield 90.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,3-diaminotoluene (5.0g, 40.9 mmol) in pyridine (40 mL) at 0° C. was added thionyl chloride (7.0 mL, 98.2 mmol) dropwise. The reaction mixture was stirred at 0° C. for 30 mins, then water (200 mL) was added. The solution was extracted with dicholomethane (2×250 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give compound 839A (5.57g) as a dark brown liquid.

Workup

  1. extractionThe solution was extracted with dicholomethane (2×250 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-973180f12602441d985451f98a8fdfbe
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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