Ammonium Hydroxide → HCID 178513941, compound

HRID 1049293Notes

Reaction equation

HRID 1049293 reaction equation
[F:1][C:2]([F:13])([F:12])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9](O)=[O:10])[CH2:5][CH2:4]1.S(Cl)(Cl)=O.[NH4+:18].[OH-]>>[F:1][C:2]([F:13])([F:12])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH2:18])=[O:10])[CH2:5][CH2:4]1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 178525710HCID 178525710, compound

Product 1

HCID 178513941HCID 178513941, compoundYield 76.3%

Procedure

A solution of trans-4-trifluoromethylcyclohexanecarboxylic acid (0.5 g, 2.55 mmol) in thionyl chloride (3.70 mL, 51.0 mmol) was heated to 60° C. for 1 h, cooled to RT and concentrated to dryness. The material was co-evaporated with toluene (2×), dissolved in EtOAc (5 mL), treated with satd. NaHCO3 (5 mL) followed by NH4OH (˜13M, 0.588 mL, ˜7.65 mmol) and stirred at RT for 0.5 h. The layers were separated, the aqueous layer extracted with EtOAc (2×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford trans-4-(trifluoromethyl)cyclohexanecarboxamide (380 mg, 76%) as a white solid.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutiondissolved in EtOAc (5 mL)
  3. additiontreated with satd
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with EtOAc (2×)
  6. dry with materialthe combined organics were dried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-580763d37bf24a9fb6f4b0963c612e87
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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