40639-93-8 → 4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-amine

HRID 415130Notes

Reaction equation

HRID 415130 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>S(=O)(=O)(O)O.CO.O>[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

4

Reactant 1

HCID 1181961540639-93-8

Product 1

HCID 123658514,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-amineYield 101.2%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

N-(4,5,6,7-Tetrahydro-1H-benzo[d]imidazol-2-yl)acetamide (0.40 g) was heated at reflux in a stirred solution of 1:1 methanol/water (5 mL) containing 5 drops of concentrated sulfuric acid for 12 hours. The mixture was cooled and evaporated to dryness on the lyophilizer to give 0.31 g of 4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-amine. 1H-NMR (400 MHz, DMSO-d6) 13.4 (bs, 1H), 6.59 (bs, 2H), 2.55 (m, 2H), 2.49 (m, 2H), 1.67 (m, 2H), 1.62 (m, 2H).

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated to dryness on the lyophilizer

Sources & evidence

ORD record
ord-55d0891e98de4ca0aed892ce8e19aa6a
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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