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

HRID 2292653Notes

Reaction equation

HRID 2292653 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]2[S: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[S: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 214793445-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzothiophene

Product 1

HCID 214793432-(N-(7-tert-Butyl-2,3-dihydro-3,3-dimethylbenzo[b]thiophene-5-yl)amino)imidazolineYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 0.33 g (1.3 mmol) solution of 5-amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzo[b]thiophene in 10 mL of acetonitrile at RT is added 0.2 g (1.3 mmol) of imidazoline-2-sulfonic acid, (Maryonoff 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 155 mg (40%) of product.

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-2299cdb92d05486f97d6ad29609114a8
Source dataset
uspto-grants-1997_11
Patent number
US05684031

Reaction notes

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