Dimethyl Sulfoxide → HCID 86645618, compound

HRID 882716Notes

Reaction equation

HRID 882716 reaction equation
CS(C)=O.Cl.[NH2:6][OH:7].C(N(CC)CC)C.[O:15]=[S:16]1(=[O:36])[C:22]2[CH:23]=[C:24]([O:27][C:28]3[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=3)[C:31]#[N:32])[CH:25]=[CH:26][C:21]=2[NH:20][CH2:19][CH2:18][NH:17]1>C(OCC)C.ClCCl.O.C1COCC1>[O:36]=[S:16]1(=[O:15])[C:22]2[CH:23]=[C:24]([O:27][C:28]3[CH:29]=[C:30]([C:31](=[N:6][OH:7])[NH2:32])[CH:33]=[CH:34][CH:35]=3)[CH:25]=[CH:26][C:21]=2[NH:20][CH2:19][CH2:18][NH:17]1

Participants

9

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 67543139HCID 67543139, compound

Product 1

HCID 86645618HCID 86645618, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 750 μl of DMSO there are added hydroxylamine hydrochloride (1.90 mmol) and then triethylamine (1.90 mmol). An abundant white precipitate is formed, which is diluted by adding 3 ml of THF and stirring is carried out for 25 minutes at ambient temperature. The THF is evaporated off under reduced pressure and the suspension is filtered. The product of Example 6 (0.317 mmol) is added to the filtrate and the solution is stirred overnight at ambient temperature. After adding water to the reaction mixture, a gum forms which is made solid by adding dichloromethane and ethyl ether. The solid is filtered off and rinsed with water and ethyl ether to yield the title product.

Workup

  1. customAn abundant white precipitate is formed
  2. additionwhich is diluted
  3. customThe THF is evaporated off under reduced pressure
  4. filtrationthe suspension is filtered
  5. stirringthe solution is stirred overnight at ambient temperature
  6. filtrationThe solid is filtered off
  7. washrinsed with water and ethyl ether

Sources & evidence

ORD record
ord-5adcf222988144bb82138cb2315b0c45
Source dataset
uspto-grants-2012_08
Patent number
US08236790B2

Reaction notes

Loading…