Acetone → HCID 178460822, compound

HRID 1733384Notes

Reaction equation

HRID 1733384 reaction equation
[NH:1]=[C:2]1[CH:7]=[CH:6][C:5]([N+:12]([O-:14])=[O:13])([S:8][CH2:9][CH2:10][CH3:11])[C:4]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:3]1[NH:22][C:23]([NH:25][C:26]([O:28][CH3:29])=[O:27])=[S:24].[CH3:30]C(C)=O.[OH-].[Na+].CI>O>[NH:1]=[C:2]1[CH:7]=[CH:6][C:5]([N+:12]([O-:14])=[O:13])([S:8][CH2:9][CH2:10][CH3:11])[C:4]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:3]1[NH:22][C:23](=[N:25][C:26]([O:28][CH3:29])=[O:27])[S:24][CH3:30]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 131711995HCID 131711995, compound

Product 1

HCID 178460822HCID 178460822, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-imino-(4-nitro)phenylmethyl-2-(3-carbomethoxythioureido)-4-propylthiobenzene (4.3 g; 0.01 mole) acetone (50 ml), water (25 ml) and 50% aqueous sodium hydroxide (0.8 g; 0.01 mole) is stirred at room temperature for 15 min. and is cooled to 12° C. To the mixture there is added methyl iodide (1.4 g; 0.01 mole) and it is stirred at 13° C. to 20° C. for 2 hrs. The suspension that forms is vacuum filtered and the filter cake is washed with acetone and dried to afford 1-imino(4-nitro)phenylmethyl-2-(3-carbomethoxy-S-methylisothioureido)-4-propylthiobenzene (3.5 g; 78%), m.p. 135°-137° C. dec.

Workup

  1. temperatureis cooled to 12° C
  2. stirringis stirred at 13° C. to 20° C. for 2 hrs
  3. filtrationfiltered
  4. washthe filter cake is washed with acetone
  5. customdried

Sources & evidence

ORD record
ord-13b00015aca342d4b60f14b287cffb6c
Source dataset
uspto-grants-1980_12
Patent number
US04241079

Reaction notes

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