2-(Isocyanatomethyl)thiophene → HCID 44128465, compound

HRID 2098296Notes

Reaction equation

HRID 2098296 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]=[C:8]=[O:9].[N+:10](=[C:12]1[N:16]=[CH:15][N:14]=[C:13]1[C:17]([NH2:19])=[O:18])=[N-:11]>CS(C)=O>[O:9]=[C:8]1[N:7]([CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[N:11]=[N:10][C:12]2=[C:13]([C:17]([NH2:19])=[O:18])[N:14]=[CH:15][N:16]12

Participants

4

Reactant 2

HCID 158906212-(Isocyanatomethyl)thiopheneHCID 534265854-Diazo-4H-imidazole-5-carboxamide

Product 1

HCID 44128465HCID 44128465, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Thiophen-2-ylmethyl isocyanate (0.350 g, 2.5 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.314 g, 2.3 mmol) in dry dimethylsulfoxide (2.5 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 (off-white) was removed by filtration, washed with water and ethyl acetate and air dried to give the title compound. Yield: 0.405 g, 64%. IR vmax/cm−1 3094, 1732, 1690, 1607. 1H NMR δH (DMSO-d6) 5.68 (2H, s, CH2Ar), 7.03 (1H, dd, J=5.1, 3.5, ArH), 7.25 (1H, dd, J=3.5, 1.0, ArH), 7.55 (1H, dd, J=5.1, 1.0, ArH), 7.71 (1H, br s, NH), 7.83 (1H, br s, NH), 8.85 (1H, s, 6-H).

Workup

  1. customThe reaction was quenched by the addition of ice
  2. customthe solid product (off-white) was removed by filtration
  3. washwashed with water and ethyl acetate and air
  4. customdried

Sources & evidence

ORD record
ord-9dd34706b0924f5dba6837bd0f905e66
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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