Dimethylamine → 3-Iodo-N,N-dimethylbenzamide

HRID 1616935Notes

Reaction equation

HRID 1616935 reaction equation
C[CH2:2][N:3]=[C:4]=NCCCN(C)C.CNC.C1COCC1.[I:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](O)=[O:25]>O>[I:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([N:3]([CH3:4])[CH3:2])=[O:25]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 120603-Iodobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 34096203-Iodo-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

EDCI (1.3 g, 6.6 mmol) was added to a solution of dimethylamine in THF (2 M, 6 mL, 10 mmol) and 3-iodobenzoic acid (1.5 g, 6 mmol). After 18 h stirring the reaction was transferred into water, and then extracted with ethyl acetate. The organic phase was dried over sodium sulfate. The solvent was evaporated to afford the product as a viscous, clear oil. The product was used in the next reaction step without further purification. MS m/z: 276 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customThe solvent was evaporated
  4. customto afford the product as a viscous, clear oil
  5. customThe product was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-e8e6b0a9456d426290f007b1fdeb991c
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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