Water → Ethyl 7-(cyanoamino)heptanoate

HRID 1729907Notes

Reaction equation

HRID 1729907 reaction equation
[NH:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]([NH2:4])=O.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>N1C=CC=CC=1>[NH:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]#[N:4]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 21501463Ethyl 7-(carbamoylamino)heptanoate

Product 1

HCID 21501476Ethyl 7-(cyanoamino)heptanoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 7-ureidoheptanoate (2.1 g., 0.01 mole) in pyridine (10 ml.) is added p-toluenesulfonylchloride (2.0 g., excess). The reaction is stirred at room temperature for two hours, poured into water (100 ml.), then extracted with ether (2 × 100 ml.). The ether is washed with 5% hydrochloric acid (2 × 25 ml.), brine, then dried over sodium sulfate. The solvent is removed in vacuo to give ethyl 7-cyanamidoheptanoate as a light yellow oil, yield 1.7 g. (86%).

Workup

  1. extractionextracted with ether (2 × 100 ml.)
  2. washThe ether is washed with 5% hydrochloric acid (2 × 25 ml.), brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-9189190da2334e40b7d187da88df09e1
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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