Ethylenediamine → N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]ethane-1,2-diamine

HRID 1436406Notes

Reaction equation

HRID 1436406 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[N:6]=1.[CH2:14]([NH2:17])[CH2:15][NH2:16].C([O-])(O)=O.[Na+]>>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([NH:16][CH2:15][CH2:14][NH2:17])[S:3][CH:4]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 516892Sodium BicarbonateHCID 685381612-Bromo-4-(4-bromophenyl)thiazole

Product 1

HCID 46769472N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]ethane-1,2-diamineYield 97.4%

Conditions

Temperature
130 °C

Procedure

2-Bromo-4-(4-bromophenyl)-1,3-thiazole (2.0 g, 6.2 mmol), prepared in step 2 of Example 1, was dissolved in ethylenediamine (10.0 mL, 185 mmol) and heated to 130° C. for 2 h. The mixture was cooled and poured into saturated NaHCO3 and extracted with ether. The ether extracts were combined and washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]ethane-1,2-diamine (1.8 g, 97%) as a yellow solid. HRMS: calcd for C11H12BrN3S+H+, 298.00080; found (ESI, [M+H]+), 298.0012. Analytical HPLC: retention time 7.0 min, 210-370 nm the Xterra® RP18 column, 3.5μ, 150×4.6 mm 40° C. 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ether
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c606c9caaf28486b8b03329e05181bbc
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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