Dimethylformamide → HCID 178513941, compound

HRID 410086Notes

Reaction equation

HRID 410086 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.O=S(Cl)Cl.C(Cl)Cl.C[N:22](C=O)C>>[F:1][C:2]([F:13])([F:12])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH2:22])=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 178525710HCID 178525710, compound

Product 1

HCID 178513941HCID 178513941, compound

Procedure

A mixture of trans-4-trifluoromethyl-cyclohexane-carboxylic acid (10.4 g, 53.1 mmol), SOCl2 (10 mL, 137 mmol), DCM (100 mL) and DMF (200 μl) is heated to reflux for 1.5 h and concentrated. The crude acid chloride is diluted with 100 mL THF and conc. NH3 (350 mL) is slowly added. It is stirred for 5 min and the mixture is concentrated and dried at 40°.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 1.5 h
  3. concentrationconcentrated
  4. additionThe crude acid chloride is diluted with 100 mL THF and conc. NH3 (350 mL)
  5. additionis slowly added
  6. concentrationthe mixture is concentrated
  7. customdried at 40°

Sources & evidence

ORD record
ord-957318bad34a45379e4498abaefde2b6
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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