Triethylamine → HCID 18788377, compound

HRID 1106468Notes

Reaction equation

HRID 1106468 reaction equation
C(N(CC)CC)C.Cl[C:9](=[O:21])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[CH2:22]([O:24][C:25]([CH:27]1[CH2:32][NH:31][C:30]2[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=2[O:28]1)=[O:26])[CH3:23]>ClCCl>[CH2:14]([O:13][C:11]([CH2:10][C:9]([N:31]1[C:30]2[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=2[O:28][CH:27]([C:25]([O:24][CH2:22][CH3:23])=[O:26])[CH2:32]1)=[O:21])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31090Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylateHCID 11148560Propanoic acid, 3-chloro-3-oxo-, phenylmethyl ester

Product 1

HCID 18788377HCID 18788377, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

54.6 mmol (7.6 ml) of triethylamine and 35.9 mmol (7.64 g) of benzyl 3-chloro-3-oxopropanoate are added to 17.1 mmol (3.53 g) of 2-ethoxycarbonyl-3,4-dihydro-2H-1,4-benzoxazine (described in J. Heterocyclic Chem., 1985, 22, 177) in 35 ml of dichloromethane. The reaction mixture is stirred at room temperature for 1 hour. After hydrolysis and extraction with dichloromethane, the organic phase is concentrated and purified by chromatography on silica gel using an ethyl acetate/petroleum ether mixture (2/8) as eluant to yield the expected compound.

Workup

  1. concentrationthe organic phase is concentrated
  2. custompurified by chromatography on silica gel using an ethyl acetate/petroleum ether mixture (2/8) as eluant

Sources & evidence

ORD record
ord-a908f0d6a2dd464aab02ff13ef5676af
Source dataset
uspto-grants-2000_05
Patent number
US06057317

Reaction notes

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