Water → 1-(Cyanoamino)nonan-4-yl acetate

HRID 1729909Notes

Reaction equation

HRID 1729909 reaction equation
[C:1]([O:4][CH:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:6][CH2:7][CH2:8][NH:9][C:10]([NH2:12])=O)(=[O:3])[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>N1C=CC=CC=1>[C:1]([O:4][CH:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:6][CH2:7][CH2:8][NH:9][C:10]#[N:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 215014481-(Carbamoylamino)nonan-4-yl acetate

Product 1

HCID 215014751-(Cyanoamino)nonan-4-yl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 4-acetoxynonylurea (2.4 g., 0.01 mole) in pyridine (10 ml.) is added p-toluene-sulfonyl chloride (2.0 g., excess) in one portion. The reaction is stirred at room temperature for six hours then poured into water (150 ml.). The aqueous mixture is extracted with ether (3 × 75 ml.), the ether is washed with 5% hydrochloric acid, brine, and dried over sodium sulfate. The solvent is removed in vacuo to give 4-acetoxynonylcyanamide as a residual oil.

Workup

  1. extractionThe aqueous mixture is extracted with ether (3 × 75 ml.)
  2. washthe ether is washed with 5% hydrochloric acid, brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-88c125c3ae62404296102bc7e732935a
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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