Hydrochloric Acid → HCID 22105677, compound

HRID 1455979Notes

Reaction equation

HRID 1455979 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14]([N:16]([C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1)[CH2:17][CH3:18])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.ClCCl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[CH2:14][N:16]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:28][CH:29]=1)[CH2:17][CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 22105552HCID 22105552, compound

Product 1

HCID 22105677HCID 22105677, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Borane-tetrahydrofuran complex (2.7 mL of a 1.0M solution in THF) was added over 5 minutes to a solution of ethyl 4-[N-(3-benzyloxy-2-thienoyl)-N-(ethyl)amino]benzoate (1.0 g) in THF (10 mL). The reaction mixture was stirred at ambient temperature for 15 minutes and then heated under reflux for 1 hour. An excess of aqueous 2N HCl was added to the cooled reaction mixture which was evaporated to dryness. The residue was made basic by the addition of aqueous potassium carbonate solution and this was extracted with diethyl ether (50 mL). The ether extract was washed with brine and dried over MgSO4. The oil obtained on removal of the solvent was subjected to chromatography on silica eluting with dichloromethane to give ethyl 4-[N-(3-benzyloxy-2-thienylmethyl)-N-(ethyl)amino]benzoate as an oil in 32% yield.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. customwas evaporated to dryness
  4. additionThe residue was made basic by the addition of aqueous potassium carbonate solution
  5. extractionthis was extracted with diethyl ether (50 mL)
  6. extractionThe ether extract
  7. washwas washed with brine
  8. dry with materialdried over MgSO4
  9. customThe oil obtained on removal of the solvent

Sources & evidence

ORD record
ord-e204d7f1d6cb400fb767d88196c44133
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

Loading…