Hydrochloric Acid → HCID 20566530, compound

HRID 848220Notes

Reaction equation

HRID 848220 reaction equation
[NH2:1][N:2]([CH2:8][CH2:9][C:10]([OH:18])([CH3:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:3](=O)[O:4]CC.[CH3:19][N:20]=[C:21]=[S:22].CC(C)([O-])C.[K+].Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[OH:18][C:10]([CH3:17])([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][CH2:8][N:2]1[C:3](=[O:4])[N:20]([CH3:19])[C:21](=[S:22])[NH:1]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11167Methyl isothiocyanateHCID 20566529HCID 20566529, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20566530HCID 20566530, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl N-amino-N-(3'-hydroxy-3-methylnonyl)carbamate (1.812 g; 6.97 mmole), and methyl isothiocyanate (764 mg; 10.5 mmole) in dry toluene (25 ml) was heated under refulx for 2 hrs and then allowed to cool to room temperature. Potassium t-butoxide (1,56 g; 13.96 mmole) was added and the mixture stirred at 25° for 16 hr. The mixture was portitioned between water (100 ml) and ethyl acetate (100 ml) and acidified with 5 M HCl. The aqueous layer was extracted with ethyl acetate (50 ml) and the combined organic layers washed with water (2×100 ml) and brine (100 ml), dried (Na2SO4), and evaporated to dryness and chromatography of the residue on Kieselgel 60 (10 g) in chloroform gave 2-(3'-hydroxy-3'-methylnonyl)-4-methyl-1,2,4-triazolidine-3-one-5-thione as a gum (1.83 g; 91%).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (50 ml)
  2. washthe combined organic layers washed with water (2×100 ml) and brine (100 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness and chromatography of the residue on Kieselgel 60 (10 g) in chloroform

Sources & evidence

ORD record
ord-837d010e0aa84cd6b5e63898b2a0db16
Source dataset
uspto-grants-1981_10
Patent number
US04294972

Reaction notes

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