Hydroxylamine → HCID 71415471, compound

A stirred solution of 33 g (0.5 m) of cyclopentadiene in 150 ml of petroleum ether was maintained at 0° to -10° C. as 23 g (0.2 m) of thiophosgene was added over 25 minutes. The colorless solution was stripped of volatiles. A solution of the residue in 200 ml of 1,2-dimethoxyethane was added over one hour at 0° C. to 2.0 m of hydroxylamine in 500 ml of water. The reaction mixture was stirred overnight and allowed to come to room temperature. A dried methylene chloride extract was stripped to yield a semi-solid residue which was purified by dry column chromatography (silica gel, ethyl ether:hexane::1:1 ). Two bands were observed. Extraction of each individually yielded 2.4 g of the less polar material, m. 87°-88° C. and 5.9 g of the more polar, m. 137°-137.5° C. The NMR and IR spectra indicate these to be the E and Z isomers of the title compound. The more polar material was identified as the Z isomer by X-ray crystallography.

1. additionwas added over 25 minutes
2. customto come to room temperature
3. extractionA dried methylene chloride extract
4. customto yield a semi-solid residue which
5. customwas purified
6. dry with materialby dry column chromatography (silica gel, ethyl ether:hexane::1:1 )
7. extractionExtraction of each individually yielded 2.4 g of the less polar material, m
8. custom87°-88° C. and 5.9 g
9. custom137°-137.5° C

ORD record

ord-579969354e2e489c870253cae66bbef5

Source dataset

uspto-grants-1984_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04424213