Sulfuric Acid → cis-1,3-Dibenzyl-4-hydroxy-4-(3-ethoxypropyl)-hexahydrothieno[3,4-d]imidazol-2-one

HRID 597600Notes

Reaction equation

HRID 597600 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6]Br)[CH3:2].[Mg].[CH2:9]([N:16]1[C@H:20]2[CH2:21][S:22][C:23](=[O:24])[C@H:19]2[N:18]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:17]1=[O:32])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.S(=O)(=O)(O)O>CCOCC.C1C=CC=CC=1.II>[CH2:9]([N:16]1[C@H:20]2[CH2:21][S:22][C:23]([OH:24])([CH2:6][CH2:5][CH2:4][O:3][CH2:1][CH3:2])[C@H:19]2[N:18]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:17]1=[O:32])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 1198171,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dioneHCID 2604931-bromo-3-ethoxypropaneHCID 5462224Magnesium

Product 1

HCID 86734588cis-1,3-Dibenzyl-4-hydroxy-4-(3-ethoxypropyl)-hexahydrothieno[3,4-d]imidazol-2-oneYield 100.5%

Reagents, catalysts & solvents 3

HCID 807IodineCatalystHCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a Grignard reagent solution prepared from 3-ethoxypropyl bromide (41.7 g), magnesium metal (shoot, 11.2 g) and iodine (0.2 g) in 110 ml of anhydrous ether and 30 ml of anhydrous benzene, a solution of cis-1,3-dibenzyl-hexahydrothieno[3,4-d]imidazole-2,4-dione ([α]D20 + 91°, 60.0 g) in 700 ml of anhydrous benzene is added with stirring for two and half hours at 25° to 40°C. The mixture is stirred and refluxed at 68° to 73° C for 5 hours. The reaction mixture is decomposed by the addition of 3N sulfuric acid (280 g) below 20°C. The organic layer is washed with water and concentrated in vacuo to give the residual oil of 76 g of cis-1,3-dibenzyl-4-hydroxy-4-(3-ethoxypropyl)-hexahydrothieno[3,4-d]imidazol-2-one. [α]D20 + 17° (C = 1 in CHCl3). IR (Nujol) 3350 cm-1 (OH); 1690 cm-1 (C = O).

Workup

  1. stirringThe mixture is stirred
  2. temperaturerefluxed at 68° to 73° C for 5 hours
  3. washThe organic layer is washed with water
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a07d8dd573f1402d8a6179f5b91b4d62
Source dataset
uspto-grants-1977_03
Patent number
US04014895

Reaction notes

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