Dimethylformamide → HCID 57656213, compound

HRID 911639Notes

Reaction equation

HRID 911639 reaction equation
[CH3:1][C:2]1([CH2:8][O:9][C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.S(Cl)(Cl)=O.C[N:24](C=O)C>>[CH3:1][C:2]1([CH2:8][O:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([NH2:24])=[O:15])=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 57656508HCID 57656508, compound

Product 1

HCID 57656213HCID 57656213, compoundYield 94%

Procedure

Add a drop of anhydrous DMF to a mixture of 4-(1-methyl-cyclohexylmethoxy)-benzoic acid (prepared by following the procedure described in Chem. Pharm. Bull. 1982, 30, 3601-3616) (1 g, 4.03 mmol) and thionyl chloride (3.5 mL) at room temperature. Stir the mixture for 1.5 h and then remove the excess of thionyl chloride in vacuo. Take-up the crude acid chloride in anhydrous THF (10 mL) and add the resulting solution to cold concentrated NH4OH (50 mL). Stir for 2.5 h at room temperature and concentrate in vacuo. Collect the solid formed via filtration and dry in vacuo to obtain the desired intermediate (0.94 g, 94%). MS (ES+) m/z: 248 (M+H)+.

Workup

  1. customprepared
  2. customat room temperature
  3. customremove the excess of thionyl chloride in vacuo
  4. additionadd the resulting solution to cold concentrated NH4OH (50 mL)
  5. stirringStir for 2.5 h at room temperature
  6. concentrationconcentrate in vacuo
  7. customCollect the solid
  8. customformed via filtration
  9. customdry in vacuo

Sources & evidence

ORD record
ord-6be8a3e6c8f14838b23e4e7f34d42563
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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