Sodium Hydroxide → HCID 12805850, compound

HRID 543482Notes

Reaction equation

HRID 543482 reaction equation
[C:1]([NH:4][C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:15])=[S:6])(=[NH:3])[NH2:2].ClN1C(=O)CCC1=O.[OH-].[Na+]>C(Cl)Cl>[NH2:3][C:1]1[N:4]=[C:5]([NH:7][C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:15])[S:6][N:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 178424819HCID 178424819, compound

Product 1

HCID 12805850HCID 12805850, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7.0 g (0.03 mole) 1-amidino-3-(2,6-dimethylphenyl)-thiourea in 150 ml methylene chloride is stirred with 4.2 g (0.03 mole) N-chlorosuccinimide (95%) for 1 hour at 20° C., then for another hour after the addition of 15 ml conc. NaOH. After dilution with water, the methylene chloride phase is separated by filtration and, by column-chromatography with silica gel (MeOH/CHCl3 : 10/90), 4.8 g 3-amino-5-(2,6-dimethylphenylamino)-1,2,4-thiadiazole having a melting point of 180° C. is obtained.

Workup

  1. customAfter dilution with water, the methylene chloride phase is separated by filtration and, by column-chromatography with silica gel (MeOH/CHCl3 : 10/90), 4.8 g 3-amino-5-(2,6-dimethylphenylamino)-1,2,4-thiadiazole having a melting point of 180° C.
  2. customis obtained

Sources & evidence

ORD record
ord-4afb397fdb384ed0b1f1f413b22962a6
Source dataset
uspto-grants-1984_05
Patent number
US04446142

Reaction notes

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