Hydrochloric Acid → Cyclopropanecarboxylic acid (3,4-dibromo-isothiazol-5-yl)-amide

HRID 2079744Notes

Reaction equation

HRID 2079744 reaction equation
[Br:1]Br.[OH-].[Na+].C([C:8]1[C:9]([Br:19])=[N:10][S:11][C:12]=1[NH:13][C:14]([CH:16]1[CH2:18][CH2:17]1)=[O:15])(=O)C.S(=O)(O)[O-].[Na+].Cl>O1CCOCC1>[Br:19][C:9]1[C:8]([Br:1])=[C:12]([NH:13][C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])[S:11][N:10]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 23665763Sodium BisulfiteHCID 66838440HCID 66838440, compound

Product 1

HCID 66838483Cyclopropanecarboxylic acid (3,4-dibromo-isothiazol-5-yl)-amideYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add bromine (118.3; mL, 2.30; mol) over 1; hour to a cooled aqueous solution of sodium hydroxide (3.77; M, 2.44; L, 9.21; mol) at 0° C. and stir 15; min. To this solution, add a solution of cyclopropanecarboxylic acid (4-acetyl-3-bromo-isothiazol-5-yl)-amide (155.7; g, 0.51; mol) in 1,4-dioxane (856.3; mL, 10.03; mol) over 100; min maintaining the temperature below 5° C. Stir for 1.5; hour maintaining the internal temperature below 10° C. Add an aqueous solution of sodium bisulfite (77.8; mL, 0.377; mol), stir for 5; min and add 12; M hydrochloric acid (390.1; mL, 4.60; mol) over 15; minutes maintaining the temperature below 25° C. Hold the mixture without stirring for 10; min then remove the supernatant, filter the remaining suspension, wash the recovered solid twice with water (200; mL) and dry under vacuum to give the title compound as a yellow solid (91.21; g, 55%). MS (m/z): 325, 327, 329; (M+1).

Workup

  1. temperaturemin maintaining the temperature below 5° C
  2. temperaturehour maintaining the internal temperature below 10° C
  3. stirringstir for 5
  4. additionmin and add 12
  5. temperatureminutes maintaining the temperature below 25° C
  6. stirringwithout stirring for 10
  7. custommin then remove the supernatant
  8. filtrationfilter the remaining suspension
  9. washwash the recovered solid twice with water (200; mL)
  10. customdry under vacuum

Sources & evidence

ORD record
ord-02aaabb4a5044b68927209b7a3036f35
Source dataset
uspto-grants-2011_04
Patent number
US07932274B2

Reaction notes

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