Water → HCID 20544857, compound

HRID 2285531Notes

Reaction equation

HRID 2285531 reaction equation
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].[CH3:7][N:8]([CH2:10][C:11]1[S:15][C:14]([CH2:16][S:17][CH2:18][CH2:19][NH:20][C:21]2[N:25]([CH3:26])[N:24]=[C:23]([NH2:27])[N:22]=2)=[CH:13][CH:12]=1)[CH3:9].C(=O)([O-])[O-].[Na+].[Na+].O>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:5])[NH:27][C:23]1[N:22]=[C:21]([NH:20][CH2:19][CH2:18][S:17][CH2:16][C:14]2[S:15][C:11]([CH2:10][N:8]([CH3:7])[CH3:9])=[CH:12][CH:13]=2)[N:25]([CH3:26])[N:24]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 54188053HCID 54188053, compound

Product 1

HCID 20544857HCID 20544857, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A cooled mixture of ethylchloroformate (0.45 g) in pyridine was treated with a solution of N5 -[2-[[[5-[(dimethylamino)methyl]-2-thienyl]methyl]thio]ethyl]-1-methyl-1H-1,2,4-triazole-3,5-diamine (0.7 g) in pyridine (8 ml). Sodium carbonate (2 g) and water (10 ml) were added and the mixture evaporated in vacuo. The residue was dissolved in water (15 ml) and extracted with hot isopropanol (30 ml). The extract was evaporated and the residue purified by column chromatography (silica:methanol:0.88 ammonia; 79:1) to give the title compound (0.48 g).

Workup

  1. customthe mixture evaporated in vacuo
  2. dissolutionThe residue was dissolved in water (15 ml)
  3. extractionextracted with hot isopropanol (30 ml)
  4. customThe extract was evaporated
  5. customthe residue purified by column chromatography (silica:methanol:0.88 ammonia; 79:1)

Sources & evidence

ORD record
ord-196961d150c24a19a6d6f3f0da50d1d7
Source dataset
uspto-grants-1982_04
Patent number
US04323566

Reaction notes

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