Isopropylamine → HCID 86662609, compound

HRID 1404724Notes

Reaction equation

HRID 1404724 reaction equation
C([Li])CCC.C(N)(C)C.[C:10]([CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].Cl[CH2:20][S:21][CH2:22]Cl>CCOCC>[C:10]([C:12]([CH3:18])([CH2:20][S:21][CH3:22])[C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 98018Ethyl 2-cyanopropionateHCID 565560Bis(chloromethyl) sulfideHCID 178418339Butyllithium

Product 1

HCID 86662609HCID 86662609, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
10 °C

Procedure

n-Butyllithium (24.2 mL, 60 mmol, 2.5 M solution in hexanes) was added to a solution of iso-propylamine (8.1 mL, 58 mmol) in dry ether (70 mL) under nitrogen at a rate needed to maintain temperature below −60° C. Upon completion, the reaction was allowed to warm to 10° C., re-cooled to −78° C. before addition of ethyl 2-cyanopropanoate (7 g, 55 mmol). After stirring at −78° C. for 90 minutes, chloromethylsulfide (4.61 mL, 55 mmol) was added and the mixture was warmed to room temperature over 14 hours, diluted with ether (350 mL), washed with water (100 mL), brine (100 mL), dried over MgSO4, concentrated under reduced pressure and distilled at 0.04 mm Hg. Yield of yellow liquid 3.95 g. (38%): by 145° C.; IR (KBr thin film) 1751 cm−1; 1H NMR (400 MHz, CDCl3) δ 4.30 (q, J=7.1 Hz, 2H), 3.08 (d, J=13.9 Hz, 1H), 2.91 (d, J=13.9 Hz, 1H), 2.30 (s, 3H), 1.67 (s, 3H), 1.35 (t, J=7.4 Hz, 3H); EIMS m/z 187.

Workup

  1. temperatureto maintain temperature below −60° C
  2. temperaturethe mixture was warmed to room temperature over 14 hours
  3. washwashed with water (100 mL), brine (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. distillationdistilled at 0.04 mm Hg
  7. customby 145° C.

Sources & evidence

ORD record
ord-1c18208b4c074cd39334e6d796ef38b7
Source dataset
uspto-grants-2014_12
Patent number
US08912338B2

Reaction notes

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