Thionyl Chloride → N-Cyclopropyl-3-iodo-4-methylbenzamide

HRID 1042636Notes

Reaction equation

HRID 1042636 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.S(Cl)(Cl)=O.CC[N:18]([CH:22]([CH3:24])[CH3:23])C(C)C.C1(N)CC1>C(Cl)Cl.CCOC(C)=O>[CH:22]1([NH:18][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([I:1])[CH:3]=2)[CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 6216403-Iodo-4-methylbenzoic acid

Product 1

HCID 21914546N-Cyclopropyl-3-iodo-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-iodo-4-methylbenzoic acid (3.5 g, 13 mmol) was added thionyl chloride (10 mL) before heating the mixture to reflux for 1.5 h. The reaction mixture was concentrated in vacuo, and dissolved in DCM (50 mL) and Hunigs base (4.6 mL, 27 mmol). After the addition of cyclopropylamine (1.87 mL, 27 mmol) at −78° C., the reaction mixture was stirred at ambient Temp. for about 3 h. The mixture was diluted with 100 mL DCM, washed with 20 mL saturated, aqueous NaHCO3 and 20 mL 3 N HCl, and dried over anhydrous Na2SO4. The solid obtained was suspended in EtOAc and filtered to give the title compound. MS (ES+): 302 (M+H)+.

Workup

  1. temperaturebefore heating the mixture
  2. temperatureto reflux for 1.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutiondissolved in DCM (50 mL)
  5. washwashed with 20 mL saturated
  6. dry with materialaqueous NaHCO3 and 20 mL 3 N HCl, and dried over anhydrous Na2SO4
  7. customThe solid obtained
  8. filtrationfiltered

Sources & evidence

ORD record
ord-efaf29e6a3b64bfc99ac3e518426f21a
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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