Phenethylamine → HCID 9837380, compound

HRID 1857973Notes

Reaction equation

HRID 1857973 reaction equation
Br[C:2]1[S:6][C:5]([NH2:7])=[N:4][N:3]=1.[CH2:8]([NH2:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.OP([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:7][C:5]1[S:6][C:2]([NH:16][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:3][N:4]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 24450Potassium Phosphate, DibasicHCID 36508832-Amino-5-bromo-1,3,4-thiadiazole

Product 1

HCID 9837380HCID 9837380, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (360 mg), phenethylamine (0.38 ml), and K2HPO4 (522 mg) in 2 ml of DMF is heated under nitrogen at 100° C. for two hours, then partitioned between water and ethyl acetate. The organic phase is washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. Flash chromatography of the residue on silica using 4-5% methanol in dichloromethane provides 261 mg of the title compound. Recrystallization of 238 mg of this from 10 ml of 1:1 acetonitrile toluene affords 205 mg of crystals.

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic phase is washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fad7622259ee44f6b4fa7d28f7152144
Source dataset
uspto-grants-2000_11
Patent number
US06150385

Reaction notes

Loading…