Methanol → 1103500-71-5

HRID 1689782Notes

Reaction equation

HRID 1689782 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]([C:9]([OH:11])=[O:10])=[N:7][S:8][C:4]=2[CH:3]=1.S(Cl)(Cl)=O.[CH3:18]O>>[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]([C:9]([O:11][CH3:18])=[O:10])=[N:7][S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 534011926-Bromobenzo(d)isothiazole-3-carboxylic acid

Product 1

HCID 669062851103500-71-5Yield 95%

Conditions

Temperature
80 °C

Procedure

To a solution of 6-bromobenzo[d]isothiazole-3-carboxylic acid (1.0 g, 3.89 mmol) in methanol (15 mL), thionyl chloride (0.92 g, 7.74 mmol) is added slowly at room temperature and the solution is stirred at 80° C. for 14 h. Cool the mixture to room temperature and concentrate to give 1.0 g (95%) of the title compound as a light brown solid. 1H NMR (400 MHz, MeOD) δ 4.04 (s, 3H), 7.73 (dd, J=8.8, 1.6 Hz, 1H), 8.41 (s, 1H), 8.61 (d, J=8.8 Hz, 1H).

Workup

  1. temperatureCool the mixture to room temperature
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-b146690378164def9c755a2e5a599f66
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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