Triethylamine → HCID 86595484, compound

HRID 851882Notes

Reaction equation

HRID 851882 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][OH:10].[O:11]=[S:12]1(=[O:34])[C:17]2[CH:18]=[C:19]([O:22][C:23]3[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=3)[C:26]#[N:27])[CH:20]=[CH:21][C:16]=2[N:15]2[CH2:31][CH2:32][CH2:33][C:14]2=[N:13]1>CS(C)=O>[O:34]=[S:12]1(=[O:11])[C:17]2[CH:18]=[C:19]([O:22][C:23]3[CH:24]=[C:25]([C:26](=[N:9][OH:10])[NH2:27])[CH:28]=[CH:29][CH:30]=3)[CH:20]=[CH:21][C:16]=2[N:15]2[CH2:31][CH2:32][CH2:33][C:14]2=[N:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 12157387HCID 12157387, compound

Product 1

HCID 86595484HCID 86595484, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

616 μl (4.42 mmol) of triethylamine are added to a solution of hydroxylamine hydrochloride (307 mg, 4.42 mmol) in 1.5 ml of DMSO and the suspension is stirred for 10 minutes. The precipitate is filtered off and the filtrate is concentrated. 250 mg (0.737 mmol) of the product obtained in Step B of Example 1 are then added to that filtrate and the solution is stirred at 75° C. for 16 hours. The reaction mixture is allowed to return to ambient temperature, and precipitation is brought about using water. A gummy white paste is observed which is made harder by adding CH2Cl2. The precipitate is filtered off to yield the title product.

Workup

  1. filtrationThe precipitate is filtered off
  2. concentrationthe filtrate is concentrated
  3. stirringthe solution is stirred at 75° C. for 16 hours
  4. customto return to ambient temperature
  5. customprecipitation
  6. additionby adding CH2Cl2
  7. filtrationThe precipitate is filtered off

Sources & evidence

ORD record
ord-0a894e369e644b6dbeeb94891a29f9b1
Source dataset
uspto-grants-2007_08
Patent number
US07253163B2

Reaction notes

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