Dimethylamine → 3-Iodo-N,N-dimethylbenzamide

HRID 518144Notes

Reaction equation

HRID 518144 reaction equation
C[CH2:2][N:3]=[C:4]=NCCCN(C)C.Cl.CNC.C1COCC1.[I:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](O)=[O:26]>O>[I:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([N:3]([CH3:4])[CH3:2])=[O:26]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 120603-Iodobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 34096203-Iodo-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

EDCl (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-e079170cf6354df8ade8699268464eb9
Source dataset
uspto-grants-2015_08
Patent number
US09115147B2

Reaction notes

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