Water → 4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-amine

HRID 1844980Notes

Reaction equation

HRID 1844980 reaction equation
[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[NH:10]C(=O)C.O.OS(O)(=O)=O>CO>[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[NH2:10]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 1181961540639-93-8

Product 1

HCID 123658514,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-amineYield 87.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 150 mg (0.83 mmol) of N-(4,5,6,7-tetrahydro-1H-benzoimidazol-2-yl)-acetamide in methanol (3 mL) was added water (3 mL) and conc. H2SO4 (0.3 mL). The mixture was heated at 100° C. under microwave (150 w, 250 psi) for 1 h. After removal of all the solvents, the residue was neutralized with sat. aq. Na2CO3 solution then diluted with methanol (50 mL). After removal of the inorganic salts through filtration, the organic phase was concentrated and dried under vacuum to afford 100 mg (86%) of the 4,5,6,7-tetrahydro-1H-benzoimidazol-2-ylamine, which was used for the next step without further purification.

Workup

  1. customAfter removal of all the solvents
  2. additionthen diluted with methanol (50 mL)
  3. customAfter removal of the inorganic salts
  4. filtrationthrough filtration
  5. concentrationthe organic phase was concentrated
  6. customdried under vacuum

Sources & evidence

ORD record
ord-4b8a67f6480a47bd99478317d7c724b8
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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