Dimethylformamide → HCID 24965466, compound

HRID 555373Notes

Reaction equation

HRID 555373 reaction equation
[CH3:1][C:2]12[CH2:27][CH:6]([N:7]([C:9]([C:11]3[CH:26]=[CH:25][C:14]([O:15][CH:16]4[CH2:21][CH2:20][CH:19]([C:22](O)=[O:23])[CH2:18][CH2:17]4)=[CH:13][CH:12]=3)=[O:10])[CH2:8]1)[CH2:5][C:4]([CH3:29])([CH3:28])[CH2:3]2.S(Cl)(Cl)=O.C[N:35](C=O)C>C(Cl)Cl>[CH3:1][C:2]12[CH2:27][CH:6]([N:7]([C:9]([C:11]3[CH:26]=[CH:25][C:14]([O:15][CH:16]4[CH2:21][CH2:20][CH:19]([C:22]([NH2:35])=[O:23])[CH2:18][CH2:17]4)=[CH:13][CH:12]=3)=[O:10])[CH2:8]1)[CH2:5][C:4]([CH3:29])([CH3:28])[CH2:3]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 24963336HCID 24963336, compound

Product 1

HCID 24965466HCID 24965466, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenoxy]-cyclohexanecarboxylic acid (4 g, 10.01 mmol) in DCM (75 mL) was added thionylchloride (1.5 mL) and dry DMF (0.5 mL). The resulting mixture was stirred for 16 hrs at room temperature and the volatiles evaporated in vacuo. The residue was dissolved in DCM (50 mL), added dropwise to an ice cooled solution of conc. aqueous ammoniac (150 mL) and TEA (7 mL) and stirred for 1 hr. The phases were separated and the organic phase dried (Na2SO4), filtered and evaporated which afforded 3.5 g (88%) of the title compound as a solid.

Workup

  1. customthe volatiles evaporated in vacuo
  2. dissolutionThe residue was dissolved in DCM (50 mL)
  3. additionadded dropwise to an ice cooled solution of conc. aqueous ammoniac (150 mL) and TEA (7 mL)
  4. stirringstirred for 1 hr
  5. customThe phases were separated
  6. dry with materialthe organic phase dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated which

Sources & evidence

ORD record
ord-67dd26d97b944f85a66be925a4fcbe40
Source dataset
uspto-grants-2011_11
Patent number
US08053447B2

Reaction notes

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