114546-13-3 → HCID 44128464, compound

HRID 2098294Notes

Reaction equation

HRID 2098294 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][N:7]=[C:8]=[O:9])=[CH:2]1.[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:3]2[CH:4]=[CH:5][S:1][CH:2]=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 15813638114546-13-3HCID 534265854-Diazo-4H-imidazole-5-carboxamide

Product 1

HCID 44128464HCID 44128464, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Thiophen-3-ylmethyl isocyanate (0.306 g, 2.2 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.274 g, 2 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) removed by filtration, washed with water and ethyl acetate and air dried. Yield: 0.235 g, 42%. IR vmax/cm−1 3094, 1728, 1688, 1604. 1H NMR δH (DMSO-d6) 5.50 (2H, s, CH2Ar), 7.17 (1H, dd, J 4.9, 1.3, ArH), 7.55-7.58 (2H, m, ArH), 7.70 (1H, br s, NH), 7.83 (1H, br s, NH), 8.85 (1H, s, 6-H). δC (DMSO-d6) 48.0, 124.4, 127.3, 128.0, 129.5, 131.4, 134.9, 136.7, 139.5, 162.0.

Workup

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

Sources & evidence

ORD record
ord-ccded55322304b299f8d2c9e114ce945
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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