Triethylamine → HCID 748373, compound

HRID 1941500Notes

Reaction equation

HRID 1941500 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.Cl.[CH2:8]([O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl.Cl>[CH2:8]([O:15][C:16]1[CH:17]=[CH:18][C:19]([NH:20][C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:5])=[CH:21][CH:22]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 27238314-Benzyloxyaniline hydrochloride

Product 1

HCID 748373HCID 748373, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

Cyclopropane carbonyl chloride (4.54 ml) was added dropwise over 5 min to a stirred solution of 4-benzyloxyaniline hydrochloride (11.8 g) and triethylamine (15.33 ml) in dichloromethane (60 ml). The reaction mixture was stirred at room temperature under nitrogen for 2 h. The solution was diluted with 2N hydrochloric acid (100 ml) and dichloromethane (200 ml). The organic layer was washed with 2N sodium carbonate (100 ml), water (100 ml), 10% brine (50 ml) and dried over anhydrous sodium sulphate. Concentration in vacuo gave a pale brown solid which was washed with diethyl ether (3×50 ml) to afford the title compound (12 g) as a white solid, m.p. 162°.

Workup

  1. washThe organic layer was washed with 2N sodium carbonate (100 ml), water (100 ml), 10% brine (50 ml)
  2. dry with materialdried over anhydrous sodium sulphate
  3. concentrationConcentration in vacuo
  4. customgave a pale brown solid which
  5. washwas washed with diethyl ether (3×50 ml)

Sources & evidence

ORD record
ord-3d475bfe8e6c42568ce7495d58baabe2
Source dataset
uspto-grants-1997_12
Patent number
US05703240

Reaction notes

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