Iodoethane → Methyl [3-(diethylamino)phenyl]carbamate

HRID 1033151Notes

Reaction equation

HRID 1033151 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1C=C([CH:10]=[CH:11][CH:12]=1)N)=[O:4].C(I)C.C(=O)([O-])[O-].[Na+].[Na+].[CH2:22]([N:24]([CH2:28][CH3:29])[C:25](=O)[CH3:26])[CH3:23]>O>[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:26]=[C:25]([CH:10]=[CH:11][CH:12]=1)[N:24]([CH2:22][CH3:23])[CH2:28][CH3:29])=[O:4]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 12703N,N-DiethylacetamideHCID 12877207Methyl (3-aminophenyl)carbamate

Product 1

HCID 19025317Methyl [3-(diethylamino)phenyl]carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4.5 g of 3-(methoxycarbonylamino)-aniline, 21.6 g of ethyl iodide, 14.4 g of sodium carbonate, and 90 ml of N,N-diethylacetamide was stirred for 1 hour at 110° C. The reaction mixture obtained was poured into 300 ml of water followed by stirring well and extracted with ethyl acetate. The extract was washed with water, dried by Glauber's salt, and the solvent was distilled off using a rotary evaporator to provide 6.0 g (yield: 100%) of an oily product.

Workup

  1. customThe reaction mixture obtained
  2. stirringby stirring well
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried by Glauber's salt
  6. distillationthe solvent was distilled off
  7. customa rotary evaporator

Sources & evidence

ORD record
ord-5ac32f655c454f3f99fb95a031ffb655
Source dataset
uspto-grants-1994_05
Patent number
US05310634

Reaction notes

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