Triethylamine → HCID 20505450, compound

HRID 1680341Notes

Reaction equation

HRID 1680341 reaction equation
[OH:1][CH:2]([CH3:7])[CH2:3][CH2:4][C:5]#[N:6].C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C1C=CC=CC=1>[CH3:15][S:16]([O:1][CH:2]([CH3:7])[CH2:3][CH2:4][C:5]#[N:6])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10796706HCID 10796706, compound

Product 1

HCID 20505450HCID 20505450, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a cooled (ice bath) stirred solution of 4-hydroxypentanonitrile (18.8 g, 0.19 mol) in benzene (100 ml) and triethyl amine (20 g, 0.198 mol) was added dropwise a solution of methanesulphonyl chloride (22.34 g 0.195 mol) in benzene (20 ml) over a period of 40 min. After addition was complete the stirring was continued for 20 min at room temperature. The solid (TEA.HCl) was filtered off and washed with benzene. The filtrate and washings were combined and concentrated in vacuo to give 37.7 g of the title compound containing approximately 12% of benzene: 1Hmr (CDCl3) δ: 7.38 (3H, benzene), 4.82 (1H, q, J=13 Hz), 3.1 (3H, s), 2.48 (2H, dt), 2.0 (2H, dt) and 1.46 ppm (3H, t, J=13 Hz); ir (neat) νmax : 2243 cm-1.

Workup

  1. temperatureTo a cooled (ice bath)
  2. additionAfter addition
  3. filtrationThe solid (TEA.HCl) was filtered off
  4. washwashed with benzene
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56918257f9f8486d9e23d132b5fb8675
Source dataset
uspto-grants-1981_06
Patent number
US04272437

Reaction notes

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