Chlorine → HCID 54078835, compound

HRID 2290999Notes

Reaction equation

HRID 2290999 reaction equation
C(S[CH:4]1[N:7]([CH:8]([C:22]([O:24][CH:25]2[CH2:30][O:29][CH2:28][O:27][CH2:26]2)=[S:23])[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:31])[CH:5]1[CH2:32][CH2:33][O:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=1)=[O:36])C.[Cl:48]Cl>C(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[Cl:48][CH:4]1[N:7]([CH:8]([C:22]([O:24][CH:25]2[CH2:30][O:29][CH2:28][O:27][CH2:26]2)=[S:23])[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:31])[CH:5]1[CH2:32][CH2:33][O:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=1)=[O:36]

Participants

5

Reactant 2

HCID 24526ChlorineHCID 54546192HCID 54546192, compound

Product 1

HCID 54078835HCID 54078835, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 6.90 g of p-nitrobenzyl 2-(4-ethylthio-3-p-nitrobenzyloxycarbonyloxyethyl-2-oxo-1-azetidinyl)-2-(1,3-dioxan-5-yl-oxythiocarbonyl)-acetate in 110 ml methylene chloride was cooled to -20° C. under a nitrogen atmosphere. A solution of chlorine in carbon tetrachloride (98 ml of 0.1M solution) was then added. The reaction mixture was stirred at -20° C. for 75 min., then allowed to warm to 0° C. and was washed successively with 75 ml saturated aqueous sodium bicarbonate solution (5° C.), 75 ml H2O (5° C.) and 75 ml saturated aqueous sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo yielding 5.97 g of crude title compound. The NMR spectraum in deuterochloroform shows absorptions at 1.5 (d, 3H); 3.4 (m, 1H); 3.8-4.14 (c, 5H); 4.75 (s, 2H); 4.98-5.5 (c, 6 H); 5.8-6.2 (c, 1H); 7.5 (m, 4H); 8.2 (m, 4H) ppm.

Workup

  1. temperatureto warm to 0° C.
  2. washwas washed successively with 75 ml saturated aqueous sodium bicarbonate solution (5° C.), 75 ml H2O (5° C.) and 75 ml saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9adb34c2eb74497694ea909d45d16b24
Source dataset
uspto-grants-1986_10
Patent number
US04619783

Reaction notes

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