Hydrochloric Acid → N-(4-hydroxynonyl)Urea

HRID 1729908Notes

Reaction equation

HRID 1729908 reaction equation
O1CCCCC1[O:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH2:11][NH2:12].Cl.[O-:19][C:20]#[N:21].[K+]>O>[OH:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH2:11][NH:12][C:20]([NH2:21])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 203276844-(2-Tetrahydropyranyloxy)nonylamine

Product 1

HCID 21501470N-(4-hydroxynonyl)Urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 4-(2-tetrahydropyranyloxy)-nonylamine (4.8 g., 0.02 mole) in water (75 ml.) is added just enough 10% hydrochloric acid to effect solution. Then potassium cyanate (1.62 g., 0.02 mole) is added and the reaction is heated gently on the steam bath for one hour, during which time an oil separates. The reaction mixture is cooled and extracted with ether (2 × 75 ml.). The ether is dried over sodium sulfate then concentrated in vacuo to give 4-hydroxynonylurea as a residual oil. The 4-hydroxynonylurea is taken up in pyridine (20 ml.) and acetic anhydride (2.0 g., 0.02 mole) is added. The reaction is stirred eight hours at room temperature then poured into water (100 ml.), and extracted with ether (2 × 100 ml.). The ether is washed with 5% hydrochloric acid, brine, and dried over sodium sulfate. Removal of the solvent in vacuo affords the subject compound as a residual oil.

Workup

  1. temperaturethe reaction is heated gently on the steam bath for one hour, during which time an oil separates
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with ether (2 × 75 ml.)
  4. dry with materialThe ether is dried over sodium sulfate
  5. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-f88ff69253ac4d5da3c9094342e53f96
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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