Hydrochloric Acid → 1-(4-t-Butylbenzyl)-3-[2-(4-methylthiazol-5-yl)ethyl]thiourea

HRID 656280Notes

Reaction equation

HRID 656280 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][CH2:8][N:9]1C(=O)C2C(=CC=CC=2)C1=O.O.NN.Cl.[C:24]([C:28]1[CH:37]=[CH:36][C:31]([CH2:32][N:33]=[C:34]=[S:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25]>CO.O1CCCC1.CN(C)C=O.ClCCl.C(N(CC)CC)C>[C:24]([C:28]1[CH:37]=[CH:36][C:31]([CH2:32][NH:33][C:34]([NH:9][CH2:8][CH2:7][C:6]2[S:5][CH:4]=[N:3][C:2]=2[CH3:1])=[S:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 148010411-Tert-butyl-4-(isothiocyanatomethyl)benzeneHCID 156700332-[2-(4-Methyl-1,3-thiazol-5-yl)ethyl]isoindole-1,3-dione

Product 1

HCID 101324561-(4-t-Butylbenzyl)-3-[2-(4-methylthiazol-5-yl)ethyl]thioureaYield 20.7%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

2-[2-(4-methylthiazol-5-yl)ethyl]isoindol-1,3-dione (3 g) was dissolved in a mixture of methanol (10 ml) and tetrahydrofuran (10 ml) and to the solution was added dropwise hydrazine hydrate (610 mg), followed by stirring for 20 hours. To the obtained solution was added 2 N aqueous hydrochloric acid solution (6 ml), and the mixture was stirred for 3 hours and concentrated under reduced pressure to obtain reaction mixture (3.5 g) as a yellow solid. The obtained mixture (140 mg) was dissolved in dimethylformamide (5 ml) and to the solution were added 4-t-butylbenzylisothiocyanate (0.2 g) and a small amount of triethylamine, followed by stirring at room temperature for 21 hours. The resulting mixture was diluted with dichloromethane, washed with water, dried, concentrated under reduced pressure, and then purified by column-chromatography (hexane/ethyl acetate=1/1) to yield the compound 14-6 (0.07 g) as a liquid.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. customto obtain
  4. stirringby stirring at room temperature for 21 hours
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. custompurified by column-chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-ed3c7081ebd3482895dca67844fe4e0a
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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