Sulfuric Acid → HCID 86631120, compound

HRID 912669Notes

Reaction equation

HRID 912669 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([NH:12][C:13]([NH2:15])=[S:14])[CH3:11].[O-]CC.[Na+].[C:20]([CH2:22][C:23](OCC)=[O:24])#[N:21].S(=O)(=O)(O)O>CCO.O>[NH2:21][C:20]1[N:12]([CH:10]([C:2]2[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)[CH3:11])[C:13](=[S:14])[NH:15][C:23](=[O:24])[CH:22]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 86631119HCID 86631119, compound

Product 1

HCID 86631120HCID 86631120, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of N-[1-(1H-benzimidazol-2-yl)ethyl]thiourea (0.33 g, 1.5 mmol, obtained from Example 9(a)) in EtOH (2 mL) was added, dropwise, sodium ethoxide (21% w/w, 1.67 mL, 4.5 mmol) and a solution of ethyl cyanoacetate (0.48 mL, 4.47 mmol) in EtOH (1 mL), while heating the reaction to 80° C. during 1 h 20 minutes. The reaction was kept at 80° C. for an additional 2 h 40 minutes. After cooling to r.t., water (50 mL) and 2M sulphuric acid was added. The formed solid was collected by filtration, washed with H2O and dried to give the title compound (0.21 g, 50%).

Workup

  1. additionwas added
  2. customthe reaction to 80° C. during 1 h 20 minutes
  3. filtrationThe formed solid was collected by filtration
  4. washwashed with H2O
  5. customdried

Sources & evidence

ORD record
ord-7b97bec5fe3c44318e2a2f39c6556547
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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