4,5-dihydro-1H-imidazole-2-sulfonic acid → 2-(N-(7-tert-Butyl-2,3-dihydro-3,3-dimethylbenzo[b]furan-5-yl)-amino)imidazoline

HRID 2292652Notes

Reaction equation

HRID 2292652 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]2[O:6][CH2:7][C:8]([CH3:10])([CH3:9])[C:4]=2[CH:3]=1.[NH:17]1[CH2:21][CH2:20][N:19]=[C:18]1S(O)(=O)=O>C(#N)C>[C:13]([C:11]1[C:5]2[O:6][CH2:7][C:8]([CH3:10])([CH3:9])[C:4]=2[CH:3]=[C:2]([NH:1][C:18]2[NH:19][CH2:20][CH2:21][N:17]=2)[CH:12]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 2745614,5-dihydro-1H-imidazole-2-sulfonic acidHCID 106804065-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

Product 1

HCID 98388672-(N-(7-tert-Butyl-2,3-dihydro-3,3-dimethylbenzo[b]furan-5-yl)-amino)imidazolineYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 0.3 g (1.3 mmol) solution of 5-amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzo[b]furan in 10 mL of acetonitrile at RT is added 0.2 g (1.3 mmol) of imidazoline-2-sulfonic acid, (Maryanoff et al., J. Org. Chem., 1986, 51, 1882). The reaction is then refluxed overnight. On cooling to RT, pure guanidine precipitates out of solution and is filtered from the solution to give 120 mg (32%) of product; mp 264° C. (decomp).

Workup

  1. temperatureThe reaction is then refluxed overnight
  2. custompure guanidine precipitates out of solution
  3. filtrationis filtered from the solution

Sources & evidence

ORD record
ord-2a6fa0210977413ab9f2d37aeb6c1db3
Source dataset
uspto-grants-1997_11
Patent number
US05684031

Reaction notes

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