Methyl isothiocyanate → HCID 9977391, compound

HRID 1587403Notes

Reaction equation

HRID 1587403 reaction equation
Cl.[NH2:2][C:3]1[S:4][C:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:7]=1.[H-].[Na+].[CH3:26][N:27]=[C:28]=[S:29]>CN(C)C=O>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[N:7]=[C:3]([NH:2][C:28]([NH:27][CH3:26])=[S:29])[S:4][C:5]=2[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11167Methyl isothiocyanateHCID 24758Sodium hydrideHCID 19757955HCID 19757955, compound

Product 1

HCID 9977391HCID 9977391, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 2-amino-4,5-bis(4-methoxyphenyl)thiazole hydrochloride (1.00 g) in N,N-dimethylformamide (5 ml) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil) (0.13 g) in N,N-dimethylformamide (5 ml) at 0° C. for 30 minutes. The reaction mixture was stirred at room temperature for 30 minutes. After methyl isothiocyanate (2.19 ml) was added dropwise to the reaction mixture, the reaction mixture was stirred at 80° C. for 5.5 hours. After allowing to cool to room temperature, the resulting precipitates were collected by filtration, washed with diisopropyl ether and diethyl ether to give 4,5-bis(4-methoxyphenyl)2-(3-methylthioureido)thiazole (0.81 g).

Workup

  1. stirringthe reaction mixture was stirred at 80° C. for 5.5 hours
  2. temperatureto cool to room temperature
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with diisopropyl ether and diethyl ether

Sources & evidence

ORD record
ord-393640b415cd47708584f7116343c954
Source dataset
uspto-grants-1993_06
Patent number
US05217971

Reaction notes

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