Hydrochloric Acid → HCID 19427168, compound

HRID 557988Notes

Reaction equation

HRID 557988 reaction equation
[C:1]([CH2:3][CH2:4][C:5]([CH2:16][CH2:17][C:18]#[N:19])([C:11]([O:13]CC)=[O:12])[C:6]([O:8]CC)=[O:7])#[N:2].C[N+](C)(C)C.[OH-].Cl>>[C:18]([CH2:17][CH2:16][C:5]([CH2:4][CH2:3][C:1]#[N:2])([C:11]([OH:13])=[O:12])[C:6]([OH:8])=[O:7])#[N:19]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 60966Tetramethylammonium hydroxideHCID 74046Diethyl bis(2-cyanoethyl)propanedioate

Product 1

HCID 19427168HCID 19427168, compoundYield 15.8%

Conditions

Temperature
0 °C

Procedure

Diethyl 2,2-bis(2-cyanoethyl)malonate (2 g, 7.51 mmol) was added to TMAH (25% in water, 10.95 g, 30.04 mmol) at room temperature. The mixture was stirred for 24 hours, and was then cooled to 0° C. A mixture of 12M HCl (2.69 cm3, 32.1 mmol) and ice (3 g) was added and the mixture was extracted with CH2Cl2 (5×50 cm3). The extracts were evaporated under vacuum to give 2,2-bis(2-cyanoethyl)malonic acid (0.25 g, 15.8%) as a colorless very viscous oil (lit decomposed. 158° C.).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with CH2Cl2 (5×50 cm3)
  3. customThe extracts were evaporated under vacuum

Sources & evidence

ORD record
ord-1e0fa169d1394842bbfa3e62951e2936
Source dataset
uspto-grants-2011_11
Patent number
US08062429B2

Reaction notes

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