Chloral Hydrate → HCID 87441566, compound

HRID 747378Notes

Reaction equation

S([O-])([O-])(=O)=O.[Na+].[Na+].Cl[C:9](Cl)(Cl)[CH:10]([OH:12])O.[C:15]([C:19]1[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[CH:21][C:20]=1[NH2:29])([CH3:18])([CH3:17])[CH3:16].Cl.[NH2:31][OH:32]>O.Cl>[C:15]([C:19]1[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[CH:21][C:20]=1[NH:29][C:10](=[O:12])/[CH:9]=[N:31]/[OH:32])([CH3:18])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium sulfate (20.75 g, 146 mmol) and chloral hydrate (2.78 g, 17 mmol) were dissolved in water (30 mL). Then a solution of 2,4-di-tert-butyl-phenylamine [prepared according to P. D. Bartlett, M. Roha, R. M. Stiles, J. Am. Chem. Soc. 1954, 76, 2349-2353] (3 g, 14.6 mmol) in water (6 mL), 25% HCl (1.9 mL), and a solution of hydroxylamine hydrochloride (3.25 g, 47 mmol) in water (8 mL) were added. The mixture was heated at 100° C. for 1 h. Extraction with ethyl acetate and chromathography on silica gel with a gradient of 0% to 25% of ethyl acetate in heptane afforded a light brown solid (1 g, 25%), which was a 1:1-mixture with formylated starting material. MS: m/z=277 (M+H).

Workup

extractionExtraction with ethyl acetate and chromathography on silica gel with a gradient of 0% to 25% of ethyl acetate in heptane

Sources & evidence

ORD record: ord-e706173e942745f19897cca02dc807fe
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396853B2

Reaction notes

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