Ethyl isocyanatoacetate → HCID 54468236, compound

HRID 1941100Notes

Reaction equation

HRID 1941100 reaction equation
[CH2:1]([O:8][NH:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:19]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:20]=[O:21]>CN(C=O)C>[C:15]([C:14]1[CH:13]=[CH:12][C:11]([CH2:10][N:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:20](=[O:21])[NH:19][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][CH:17]=1)#[N:16]

Participants

4

Reactant 2

HCID 76283Ethyl isocyanatoacetateHCID 21459757HCID 21459757, compound

Product 1

HCID 54468236HCID 54468236, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

2.73 g (11 mmol) of 4-(benzyloxyaminomethyl)benzonitrile are dissolved in 75 ml of DMF and added dropwise at 0° C. to a solution of 1.48 g of ethyl isocyanatoacetate in 75 ml of DMF. The mixture is heated at 50° C. for 3 d, then concentrated in vacuo. The residue is taken up in ethyl acetate and the solution is washed with water. The organic phase is dried (MgSO4) and concentrated in vacuo. The residue is dissolved in a little ethyl acetate and precipitated with ether/petroleum ether. The precipitate produced is reacted without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. washthe solution is washed with water
  3. dry with materialThe organic phase is dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue is dissolved in a little ethyl acetate
  6. customprecipitated with ether/petroleum ether
  7. customThe precipitate produced
  8. customis reacted without further purification

Sources & evidence

ORD record
ord-75cfda58637443399d62674609143b36
Source dataset
uspto-grants-1997_12
Patent number
US05703050

Reaction notes

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