Triethylamine → HCID 11456665, compound

HRID 546277Notes

Reaction equation

HRID 546277 reaction equation
[C:1]1([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:8][CH2:9][CH2:10][NH:11][C:12](=[O:15])[CH2:13]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:30]([CH2:33][CH3:34])CC)C>ClCCl>[C:1]1([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:8][CH2:9][CH2:10][NH:11][C:12](=[O:15])[CH2:13][NH:30][CH2:33][CH2:34][S:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 58040950HCID 58040950, compound

Product 1

HCID 11456665HCID 11456665, compoundYield 118.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 12.7 g (32 mmol) the compound 10 and 10.2 g (32 mmol) the compound 9 into 60 mL dichloromethane. Then add 6.7 mL (48 mmol) triethylamine followed by a heat flow process for two days. After cooling, wash with 60 mL Sodium hydrogen carbonate aqueous solution, and wash again with 60 mL water, take the organic layer. The organic phase is dried by Na2SO4, condensed and then purified by liquid chromatography (SiO2, ethyl acetate: hexane=1:1) to get light yellow oil product 11 (12.9 g, 59.9%).

Workup

  1. temperatureAfter cooling
  2. washwash with 60 mL Sodium hydrogen carbonate aqueous solution
  3. washwash again with 60 mL water
  4. dry with materialThe organic phase is dried by Na2SO4, condensed
  5. custompurified by liquid chromatography (SiO2, ethyl acetate: hexane=1:1)

Sources & evidence

ORD record
ord-d2b1084b965343edbf5a4660e011b962
Source dataset
uspto-grants-2011_05
Patent number
US07935833B2

Reaction notes

Loading…