Benzene → Diethyl 1-benzyl-4-oxoazetidine-2,2-dicarboxylate

HRID 1903014Notes

Reaction equation

HRID 1903014 reaction equation
[CH2:1]([N:8]([CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C1C=CC=CC=1.Cl>O>[CH2:1]([N:8]1[C:9](=[O:12])[CH2:10][C:13]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13505937HCID 13505937, compound

Product 1

HCID 13505935Diethyl 1-benzyl-4-oxoazetidine-2,2-dicarboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

34.1 g. (0.1 moles) of diethyl N-benzyl-N-(chloroacetyl)-amino-malonate prepared according to Example 19 and 18.2 ml. (13.2 g., 0.13 moles) of triethyl amine in 100 ml. of benzene are stirred at room temperature for 8 hours. The mixture is shaken with 100 ml. of water, 50 ml. of a 10% aqueous hydrochloric acid solution and again with 100 ml. of water. The organic phase is dried with magnesium sulfate, filtered and from the filtrate benzene is distilled off. The oily residue is distilled at 149° to 150° C., under a pressure of 0.1 mmHg. 23 g. (75%) of the named compound are obtained.

Workup

  1. dry with materialThe organic phase is dried with magnesium sulfate
  2. filtrationfiltered and from the filtrate benzene
  3. distillationis distilled off
  4. distillationThe oily residue is distilled at 149° to 150° C., under a pressure of 0.1 mmHg

Sources & evidence

ORD record
ord-e326b14dd8a44215accfb5ea883d9eb2
Source dataset
uspto-grants-1984_03
Patent number
US04435322

Reaction notes

Loading…