Acetic Acid → Methyl 7-[1-(4-hydroxynonyl)thioureido]heptanoate

HRID 1729929Notes

Reaction equation

HRID 1729929 reaction equation
[N+](=[CH2:3])=[N-].[OH:4][CH:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:6][CH2:7][CH2:8][N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:10]([NH2:12])=[S:11].C(O)(=O)C>CCOCC>[OH:4][CH:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:6][CH2:7][CH2:8][N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:3])=[O:20])[C:10]([NH2:12])=[S:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 539682077-[Carbamothioyl(4-hydroxynonyl)amino]heptanoic acid

Product 1

HCID 54187960Methyl 7-[1-(4-hydroxynonyl)thioureido]heptanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diazomethane (approx. 2.5 g., 0.06 mole) in ether (100 ml.) is mixed with a solution of 7-[1-(4-hydroxynonyl)thioureido]heptanoic acid (10.3 g., 0.03 mole) (Example 3) in ether (50 ml.). The resulting solution is allowed to stand at room temperature for 4 hours. Then acetic acid is added to destroy the excess diazomethane and the solution is washed with dilute sodium bicarbonate solution, brine, then dried over sodium sulfate. Evaporation of volatile materials at reduced pressure yields methyl 7-[1-(4-hydroxynonyl)thioureido]heptanoate as a viscous oil.

Workup

  1. customto destroy the excess diazomethane
  2. washthe solution is washed with dilute sodium bicarbonate solution, brine
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of volatile materials at reduced pressure

Sources & evidence

ORD record
ord-75d67244c68a494f9afda79b78c10e10
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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