3-(2-Chloroethyl)-1-(1,2,3,4-tetrahydro-1-naphthyl)urea → HCID 21393499, compound

HRID 1606700Notes

Reaction equation

HRID 1606700 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:6].CC(C)([O-])C.[K+]>O1CCCC1>[CH:8]1([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 989803-(2-Chloroethyl)-1-(1,2,3,4-tetrahydro-1-naphthyl)ureaHCID 23665647Potassium tert-butoxide

Product 1

HCID 21393499HCID 21393499, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3.8 grams (0.015 mole) of 1-(2-chloroethyl)-3-(1,2,3,4-tetrahydro-1-naphthyl)urea in 75 ml. dry tetrahydrofuran is added dropwise a solution of 2.25 grams (0.02 mole) of potassium tert-butoxide in 50 ml. of dry tetrahydrofuran under a nitrogen atmosphere. The reaction is then allowed to proceed at ambient temperature overnight. The mixture is then evaporated at reduced pressure. The residue is partitioned between water and ether. The ether layer is washed with water, dried, sodium sulfate, and evaporated at reduced pressure. Crystallization of the residue from acetone-ether-hexane gives 0.70 gram of product, melting point 134° C. to 139.5° C. Recrystallization from acetone-hexane gives the analytical sample, melting point 138° C. to 141.5° C. Analysis calculated for C13H16N2O: C, 72.19; H, 7.46; N, 12.95. Found: C, 72.04; H, 7.43; N, 12.89.

Workup

  1. customThe mixture is then evaporated at reduced pressure
  2. customThe residue is partitioned between water and ether
  3. washThe ether layer is washed with water
  4. customdried
  5. customsodium sulfate, and evaporated at reduced pressure
  6. customCrystallization of the residue from acetone-ether-hexane

Sources & evidence

ORD record
ord-b822345cb4744d61b1ac258209dd250c
Source dataset
uspto-grants-1976_04
Patent number
US03953506

Reaction notes

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