Ethanol → HCID 178440759, compound

HRID 1586086Notes

Reaction equation

HRID 1586086 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].OS([O-])=O.[Na+].Cl.Cl.[NH2:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[NH2:30])[C:24]([NH2:26])=[NH:25].C(O)C>O>[CH3:2][C:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]2[NH:30][C:29]3[CH:28]=[CH:27][C:23]([C:24](=[NH:25])[NH2:26])=[CH:22][C:21]=3[N:20]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 703244-tert-ButylbenzaldehydeHCID 21217850HCID 21217850, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 178440759HCID 178440759, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To 4-tert-butylbenzaldehyde (0.4000 g, 0.00247 mol) was added 3 mL of 40% NaHSO3 (aq). The mixture was stirred for 2 h at 25° C. 3,4-Diaminobenzamidine dihydrochloride (0.56 g, 0.0025 mol) and ethanol (8 mL) were added. The mixture was refluxed for 3 h. The reaction was then poured into water. The precipitate filtered and recrystallized from 2N HCl to afford 1H-benzimidzole-5-carboximidamide, 2-[4-(1,1-dimethylethyl)phenyl]- (400 mg, 44%) as a white solid: 1H NMR (DMSO-d6) δ9.47 (bs, 2 NH), 9.15 (bs, 2 NH), 8.30 (d, 2 arom-H, J=8 Hz), 8.21 (s, 1 arom-H), 7.88 (d, 1 arom-H, J=8 Hz), 7.73 (d, 1 arom-H, J=9 Hz), 7.68 (d, 2 arom-H, J=8 Hz), 1.35 (s, 9 tert-butyl-H).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. filtrationThe precipitate filtered
  3. customrecrystallized from 2N HCl
  4. customto afford 1H-benzimidzole-5-carboximidamide

Sources & evidence

ORD record
ord-26a54a565a9747b1a9a83b4a5c6fe192
Source dataset
uspto-grants-1999_08
Patent number
US05942532

Reaction notes

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