Sulfuric Acid → HCID 14856650, compound

HRID 1655623Notes

Reaction equation

HRID 1655623 reaction equation
[CH2:1]([N:8]1[CH:12]([CH2:13][S:14][CH2:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]([OH:24])[N:10]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:9]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([C:36]1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=C[CH:41]=1)C.S(=O)(=O)(O)O.[OH-].[K+]>C(O)C.CCOC(C)=O.CCCCCC>[CH2:1]([N:8]1[CH:12]([CH2:13][S:14][CH2:15][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:11]([O:24][CH2:36][CH3:41])[N:10]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:9]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 14797Potassium HydroxideHCID 14856647HCID 14856647, compound

Product 1

HCID 14856650HCID 14856650, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 2.12 g (4 RS, 5 R)-1,3-dibenzyl-2-oxo-5-(4-oxo-4-phenyl-2-thiabutyl)imidazolidin-4-ol (prepared according to Example 3) and 100 ml of ethanol is brought to pH 3.1 (against Methyl Orange) at 0°-5° C. using 2 normal sulfuric acid in ethanol. After stirring at 0°-5° C. for two hours, the mixture is brought to pH 5 to 6 using 2% potassium hydroxide in ethanol. After customary working-up and flash chromatography, 2.043 g (91% of theory) of (4 RS, 5 R)-1,3-dibenzyl-2-oxo-5-(4-oxo-4-phenyl-2-thiabutyl)-4-ethoxyimidazolidine, Rf =0.69 (EtOAc/hexane 3:7), are obtained. The following are oxo-7-(methoxycarbonyl)-2-thiaheptyl)-4-ethoxyimidazolidine, yield 85% of theory, Rf =0.62 (EtOAc/hexane 1:1),

Sources & evidence

ORD record
ord-db261b774a6f427ab6c2689174032dc2
Source dataset
uspto-grants-1993_10
Patent number
US05250699

Reaction notes

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