37441-16-0 → HCID 44128653, compound

HRID 2098303Notes

Reaction equation

HRID 2098303 reaction equation
[N:1]([CH2:4][CH2:5][S:6][CH3:7])=[C:2]=[O:3].[N+:8](=[C:10]1[N:14]=[CH:13][N:12]=[C:11]1[C:15]([NH2:17])=[O:16])=[N-:9]>CS(C)=O>[CH3:7][S:6][CH2:5][CH2:4][N:1]1[C:2](=[O:3])[N:14]2[CH:13]=[N:12][C:11]([C:15]([NH2:17])=[O:16])=[C:10]2[N:8]=[N:9]1

Participants

4

Reactant 2

HCID 1787232937441-16-0HCID 534265854-Diazo-4H-imidazole-5-carboxamide

Product 1

HCID 44128653HCID 44128653, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-Isocyanato-2-methylsulfanyl-ethane (1.09 g, 9.31 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.5 g, 3.65 mmol) in dry dimethylsulfoxide (5 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature overnight. The reaction was quenched by the addition of ice and the solid product (brown) was removed by filtration, washed with Et2O, and purified using flash chromatography (SiO2) using MeCN:CH2Cl2 (0-100% MeCN) Yield: 52 mg, 26%. 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.87 (1H, s), 7.80 (1H, s), 7.66 (1H, s), 4.48 (2H, t), 2.94 (2H, t).

Workup

  1. customThe reaction was quenched by the addition of ice
  2. customthe solid product (brown) was removed by filtration
  3. washwashed with Et2O
  4. custompurified

Sources & evidence

ORD record
ord-8be1f7dbadd54db2b4922f226690c6d1
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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