Ethanol → HCID 21915034, compound

HRID 2117937Notes

Reaction equation

HRID 2117937 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:26][C:27](=[O:29])[CH3:28])[S:14][C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:5][CH:4]=1.[Na].O.C(O)C.C[N:36](C)C=O>Cl.CO>[NH2:36][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:26][C:27](=[O:29])[CH3:28])[S:14][C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 702EthanolHCID 962WaterHCID 6228DimethylformamideHCID 5360545SodiumHCID 21914704HCID 21914704, compound

Product 1

HCID 21915034HCID 21915034, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of N-{4-{2-[4-(bromomethyl)phenyl]ethyl}-5-[4-(methylsulfonyl)phenyl]-1,3-thiazol-2-yl}acetamide (70 mg) in N,N-dimethylformamide (1 ml) was added diformimide sodium salt (13.5 mg), and the mixture was stirred for 10 min at 20° C. To the reaction mixture was added water, the mixture was extracted with ethyl acetate, washed with water twice, dried over magnesium sulfate, and evaporated to give a crude diformimide compound. The diformimide compound was suspended in conc. hydrocloric acid (200 μl), ethanol (2 ml) and methanol (0.5 ml). The reaction mixture was stirred at 20° C. for 3 hrs., then at 50° C. for 3 hrs. The volatails were evaporated. To the residue was added saturated sodium hydrogen carbonate aqueous solution, the mixture was extracted with chloroform, dried over maganesium sulfate and evaporated to give crude N-{4-(2-{4-[aminomethyl]phenyl}ethyl)-5-[4-(methylsulfonyl)phenyl]-1,3-thiazol-2-yl}acetamide, that was used as crude in the next reaction.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with water twice
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give a crude diformimide compound
  6. stirringThe reaction mixture was stirred at 20° C. for 3 hrs
  7. wait, then at 50° C. for 3 hrs
  8. customThe volatails were evaporated
  9. additionTo the residue was added saturated sodium hydrogen carbonate aqueous solution
  10. extractionthe mixture was extracted with chloroform
  11. dry with materialdried over maganesium sulfate
  12. customevaporated

Sources & evidence

ORD record
ord-6383bfa87f9f4be3aa6390ff3b1c7d69
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

Loading…