Cyclopropylamine → 4-chloro-N-cyclopropyl-3-iodoBenzamide

HRID 2357592Notes

Reaction equation

HRID 2357592 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[I:11].C([N:15]([CH:18]([CH3:20])[CH3:19])CC)(C)C.C1(N)CC1>S(Cl)(Cl)=O.CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:15][CH:18]2[CH2:20][CH2:19]2)=[O:8])=[CH:4][C:3]=1[I:11]

Participants

6

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 27576164-Chloro-3-iodobenzoic acid

Product 1

HCID 397175964-chloro-N-cyclopropyl-3-iodoBenzamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Procedure

4-Chloro-3-iodobenzoic acid (9.00 g, 31.9 mmol) was heated to 75° C. in thionyl chloride (15 mL) for 4 h. The reaction mixture became homogeneous and was concentrated and dried azeotropically with toluene. The mixture was dissolved in 1,4-dioxane (10 mL), and diisopropylethylamine (11 mL mL, 64 mmol), and cyclopropylamine (2.45 mL, 35 mmol) and stirred at ambient temperature for about 2 h. The reaction was diluted with 50 mL of EtOAc, added to an addition funnel and partitioned with 3 N HCl (aqueous). The organic layers were combined, washed 2 times with 50 mL of 3 N HCl (aqueous), and 2 times with 50 mL of sodium bicarbonate, dried over sodium sulfate, and concentrated via rotovap to give the title compound. Found MS (ES+): 322(M+H)+.

Workup

  1. concentrationwas concentrated
  2. dry with materialdried azeotropically with toluene
  3. dissolutionThe mixture was dissolved in 1,4-dioxane (10 mL)
  4. additionadded to an addition funnel
  5. custompartitioned with 3 N HCl (aqueous)
  6. washwashed 2 times with 50 mL of 3 N HCl (aqueous), and 2 times with 50 mL of sodium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-7883734289fd4f13937ee5319b60e616
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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