Chloroform → HCID 178526560, compound

HRID 79242

Reaction equation

HRID 79242 reaction equation
C([O-])(=O)C.[Na+].[N+:6]([C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][NH:13]2)([O-:8])=[O:7].C(Cl)(Cl)Cl.[Br:22]Br>C(O)(=O)C>[Br:22][C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[CH:17][C:9]=2[N+:6]([O-:8])=[O:7])[NH:13][N:12]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 180574-NitroindazoleHCID 24408BromineHCID 517045Sodium Acetate

Product 1

HCID 178526560HCID 178526560, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Sodium acetate (52.8 g, 644 mmol) and 4-nitro-1H-indazole (100 g, 613 mmol) were mixed with acetic acid (1000 mL) and chloroform (1000 mL) in a 5 L 4-neck flask with mechanical stirring. A solution of bromine (103 g, 644 mmol) in acetic acid (120 mL) was added over approximately 3.5 hours, while keeping the temperature below 21° C. After the addition was completed, the reaction mixture was stirred for an additional 2 hours. The reaction mixture was concentrated under reduced pressure. Water (2000 mL) was added to the residue. The yellow solids were collected by filtration and washed with water (3×1000 mL). The solids were air-dried on the filter and then under vacuum at 40° C. to give the desired product (129 g) as a yellow solid.

Workup

  1. customthe temperature below 21° C
  2. additionAfter the addition
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionWater (2000 mL) was added to the residue
  5. filtrationThe yellow solids were collected by filtration
  6. washwashed with water (3×1000 mL)
  7. customThe solids were air-dried on the
  8. filtrationfilter

Sources & evidence

ORD record
ord-20188b337dbc41338ecb8a954ab12147
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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