Triethylamine → HCID 20505450, compound

HRID 355243Notes

Reaction equation

HRID 355243 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, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent4×

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 compond 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
  6. customto give 37.7 g of the title

Sources & evidence

ORD record
ord-259fa0a336054b9d86e2988cd600e571
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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