4-Amino-1-methylbenzimidazole → 1-(4-Methoxy-pyridin-3-yl)-3-(1-methyl-1H-benzoimidazol-4-yl)-thiourea

HRID 405677Notes

Reaction equation

HRID 405677 reaction equation
[NH2:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH3:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[N:12]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[O:21][CH3:22])=[C:13]=[S:14]>CN(C=O)C>[CH3:22][O:21][C:20]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[NH:12][C:13]([NH:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH3:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1)=[S:14]

Participants

4

Reactant 2

HCID 15019774-Amino-1-methylbenzimidazoleHCID 866653953-Isothiocyanato-4-methoxypyridine

Product 1

HCID 866654151-(4-Methoxy-pyridin-3-yl)-3-(1-methyl-1H-benzoimidazol-4-yl)-thiourea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-amino-1-methylbenzimidazole (0.100 g, 0.679 mmol) and 3-isothiocyanato-4-methoxy-pyridine (0.113 mg, 0.680 mmol, example 4, step a) in DMF was stirred at room temperature for 64 hours. After removal of DMF in vacuo, the residue was treated with water. The precipitated solid was filtered, washed with water, and dried to give a portion of the title compound. The filtrate was concentrated and the oily brown residue was dried under vacuum to provide a second potion of the title compound.

Workup

  1. customAfter removal of DMF in vacuo
  2. additionthe residue was treated with water
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8d939e69824a42b5b2e66f99876139fd
Source dataset
uspto-grants-2014_06
Patent number
US08753857B2

Reaction notes

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