Phenethylamine → 2-[(6-chloro-3-hydroxy-2,2-dimethylchroman-4-yl)methanesulfonylamino]-N-phenethylacetamide

HRID 618826Notes

Reaction equation

HRID 618826 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH:6]([OH:14])[CH:5]2[CH2:15][S:16]([NH:19][CH2:20][C:21](O)=[O:22])(=[O:18])=[O:17].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:36]([NH2:44])[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1.CC(=O)OCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:12])([CH3:13])[CH:6]([OH:14])[CH:5]2[CH2:15][S:16]([NH:19][CH2:20][C:21]([NH:44][CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:22])(=[O:18])=[O:17]

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 21848666HCID 21848666, compound

Product 1

HCID 218486612-[(6-chloro-3-hydroxy-2,2-dimethylchroman-4-yl)methanesulfonylamino]-N-phenethylacetamideYield 87.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.5 g (1.37 mmol) of [(6-chloro-3-hydroxy-2,2-dimethylchroman-4-yl)methanesulfonylamino]acetic acid and 0.27 g (1.65 mmol) of CDI in 7 ml of THF was stirred at RT for 3 h. 0.33 g (2.75 mmol) of phenethylamine was then added and the reaction mixture was stirred overnight. After stripping off the solvent, the residue was taken up in EA and washed with dil. hydrochloric acid and water. After purification through a short chromatography column, 0.56 g of 2-[(6-chloro-3-hydroxy-2,2-dimethylchroman-4-yl)methanesulfonylamino]-N-phenethylacetamide was obtained; m.p. 168-170° C.

Workup

  1. washwashed with dil. hydrochloric acid and water
  2. customAfter purification through a short chromatography column

Sources & evidence

ORD record
ord-4967f8b1539c4ca4a4837ebd9f689d67
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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