Phosgene → 1-Azetidinecarbonyl chloride, 3-[(4-chlorophenyl)thio]-

HRID 2081386Notes

Reaction equation

[C:1]([Cl:4])(Cl)=[O:2].C(=O)([O-])[O-].[K+].[K+].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH:19]2[CH2:22][N:21](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:20]2)=[CH:14][CH:13]=1>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([S:18][CH:19]2[CH2:22][N:21]([C:1]([Cl:4])=[O:2])[CH2:20]2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred mixture of 8.5 g (0.086 mole) of phosgene and 12 g (0.086 mole) of potassium carbonate in 200 ml of methylene chloride was cooled in a water bath under nitrogen atmosphere while 26.3 g (0.072 mole) of 3-[(4-chlorophenyl)thio]-1-diphenylmethylazetidine in 100 ml of methylene chloride was added dropwise. After the addition, the reaction mixture was stirred for 20 hr then treated with enough ice to form a thick paste. The methylene chloride solution was decanted, filtered through Whatman phase separating paper and concentrated in vacuo. The residue (40 g) was triturated 3 times at -78° C. with 30/60 petroleum ether and allowed to warm to 0° C. before decanting the petroleum ether. The fine granular solid which remained was collected by filtration to yield 14.1 g (75%) of crude product. A sample was recrystallized from hexanes for analysis, m.p. 47°-48° C.

Workup

additionwas added dropwise
additionAfter the addition
additionthen treated with enough ice
customto form a thick paste
customThe methylene chloride solution was decanted
filtrationfiltered through Whatman phase
customseparating paper
concentrationconcentrated in vacuo
customThe residue (40 g) was triturated 3 times at -78° C. with 30/60 petroleum ether
custombefore decanting the petroleum ether
filtrationThe fine granular solid which remained was collected by filtration

Sources & evidence

ORD record: ord-198fd23ff78a4ae29aecebb8162a1521
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05183902

Reaction notes

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