Trichloroacetic Acid → HCID 18323957, compound

HRID 1251371Notes

Reaction equation

HRID 1251371 reaction equation
Cl[C:2](Cl)(Cl)[C:3](O)=O.[N-:8]=[N+:9]=[N-:10].[Na+].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[Mg]Br.[OH-].[NH4+]>C(Cl)(Cl)Cl>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:2]1([N:8]=[N+:9]=[N-:10])[CH2:3][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 6421Trichloroacetic AcidHCID 14923Ammonium HydroxideHCID 33557Sodium AzideHCID 178418438HCID 178418438, compound

Product 1

HCID 18323957HCID 18323957, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
10 °C

Procedure

Trichloracetic acid (31.9 g, 195 mmoles) is dissolved in chloroform (200 ml). Sodium azide (8.45 g, 130 mmoles) is added and the medium is cooled down to 10° C. The alcohol obtained in Stage 17a (11.8 g, 65 mmoles) dissolved in chloroform (50 ml) is added dropwise. The reaction medium is agitated for 48 hours whilst maintaining the temperature at 10-12° C. A solution of ammonium hydroxide (10%) is then added until neutralisation, then the aqueous phase is extracted with dichloromethane (3×100 ml). The organic phase is washed with water (200 ml), dried over Na2SO4 and concentrated to dryness. In this way, a brown oil is obtained which is then used without further purification.

Workup

  1. additionis added dropwise
  2. temperaturewhilst maintaining the temperature at 10-12° C
  3. extractionthe aqueous phase is extracted with dichloromethane (3×100 ml)
  4. washThe organic phase is washed with water (200 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customIn this way, a brown oil is obtained which
  8. customis then used without further purification

Sources & evidence

ORD record
ord-ef288b3d68024e3d9b712f919e9ac871
Source dataset
uspto-grants-2002_01
Patent number
US06342511B1

Reaction notes

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