Phenethylamine → HCID 86591261, compound

HRID 584947Notes

Reaction equation

HRID 584947 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21](O)=[O:22])[CH:16]=3)=[CH:11][CH:10]=2)[S:3]1.ON1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2N=N1.C(CN)C1C=CC=CC=1.[CH:43]1([N:49]=[C:50]=NC2CCCCC2)CCCCC1>O.CN(C)C=O>[CH2:43]([N:49]([CH3:50])[C:21]([C:17]1[CH:16]=[C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH:8]=[C:4]3[S:3][C:2](=[O:1])[NH:6][C:5]3=[O:7])=[CH:14][CH:13]=2)[CH:20]=[CH:19][CH:18]=1)=[O:22])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 1001PhenethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 86591254HCID 86591254, compound

Product 1

HCID 86591261HCID 86591261, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

500 mg (1.54 mmol) of 4′-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-carboxylic acid (prepared in Example 23(c)), 5 ml of dimethylformamide, 230 mg (1.7 mmol) of 1-hydroxybenzotriazole and 200 μl (1.5 mmol) of benzylmethylamine are introduced into at three-necked flask under a stream of nitrogen. At 0° C., 350 mg (1.7 mmol) of dicyclohexylcarbodiimide are added portionwise. The mixture is stirred for 18 hours while allowing the temperature to rise. The reaction medium is immersed in water, extracted with ethyl acetate, dried over magnesium sulfate, filtered and evaporated. The residue obtained is washed with dichloromethane and filtered. 400 mg (61%) of the desired product are obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. washis washed with dichloromethane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-2258be28829f4548848e3095cf2df772
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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