Triethylamine → HCID 20505010, compound

HRID 1701992Notes

Reaction equation

HRID 1701992 reaction equation
[C:1]1([NH:7][C:8](=[NH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:17][C:18](=O)[CH2:19][C:20]([OH:22])=[O:21].C[Si](C)(C)N[Si](C)(C)C.[CH2:33](N(CC)CC)[CH3:34]>C(OCC)(=O)C>[C:1]1([N:7]2[CH:17]=[C:18]([CH2:19][C:20]([O:22][CH2:33][CH3:34])=[O:21])[N:15]=[C:8]2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13838HexamethyldisilazaneHCID 119720Butanoic acid, 4-chloro-3-oxo-HCID 178511972HCID 178511972, compound

Product 1

HCID 20505010HCID 20505010, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9.8 g of N-phenylbenzamidine [prepared according to Org. Synth. Coll. IV: 769 (1963)], 8.25 g of the ethyl ester of 4-chloroacetoacetic acid, 100 ml of hexamethyldisilazane, and 7 ml of triethylamine was heated overnight under reflux. The mixture was then diluted with 400 ml of ethyl acetate and washed five times with saturated sodium bicarbonate solution as well as water. After extraction of the aqueous phases with methylene chloride, the combined organic phases were dried and concentrated under vacuum. The residue was purified by column chromatography on silica gel with methylene chloride/0.2-1% isopropanol as well as toluene/40% ethyl acetate as the eluent. Yield: 9.1 g (59%) of the title compound.

Workup

  1. temperaturewas heated overnight
  2. temperatureunder reflux
  3. washwashed five times with saturated sodium bicarbonate solution as well as water
  4. extractionAfter extraction of the aqueous phases with methylene chloride
  5. customthe combined organic phases were dried
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography on silica gel with methylene chloride/0.2-1% isopropanol as well as toluene/40% ethyl acetate as the eluent

Sources & evidence

ORD record
ord-973320558a68483abc0626004b7b44b0
Source dataset
uspto-grants-1983_04
Patent number
US04379927

Reaction notes

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