Water → HCID 19088328, compound

HRID 1463763Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([C:22]([NH2:24])=O)[C:19]([NH2:21])=O.O.[OH-].[Na+]>C1COCC1>[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([CH2:19][NH2:21])[CH2:22][NH2:24]

Participants

Conditions

Temperature: 0 °C

Procedure

6.8 g (0.18 mol) of lithium aluminium hydride were added with exclusion of moisture to 400 ml of absolute THF in a 1000-ml round-bottomed flask with reflux condenser and dropping funnel. Next, 15.5 g (0.06 mol) of the substituted malonic acid amide [18] in 100 ml absolute THF was slowly added dropwise and reflux-heated for 4 hours, then cooled to 0° C. 8 ml of water was carefully added followed by 6 ml of 20% caustic soda solution and a further 30 ml of water. The mixture was filtered and the remaining precipitate was twice extracted by boiling with THF. The combined filtrates were washed with saturated common-salt solution and dried over sodium sulphate. The solvent was removed in the rotary evaporator and the residue was distilled in vacuo.

Workup

temperaturewith reflux condenser
temperaturereflux-heated for 4 hours
filtrationThe mixture was filtered
extractionthe remaining precipitate was twice extracted
washThe combined filtrates were washed with saturated common-salt solution
dry with materialdried over sodium sulphate
customThe solvent was removed in the rotary evaporator
distillationthe residue was distilled in vacuo

Sources & evidence

ORD record: ord-bf68c6390c9d4b17b2d22e2e6833cac0
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05302370

Reaction notes

Loading…