Hydrochloric Acid → N-cyanohexadecanamide

HRID 1608113

반응식

HRID 1608113 반응식
[C:1](Cl)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1COCC1.[N:24]#[C:25][NH2:26].[Na].Cl>O>[C:1]([NH:26][C:25]#[N:24])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8206Palmitoyl chlorideHCID 57375518Cyanamidnatrium

생성물 1

HCID 180884N-cyanohexadecanamide수율 96.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of palmitoyl chloride (5.5 g, 0.020 mol) in 50 mol of freshly distilled dry THF was added drop-wise to a suspension of sodium cyanamide (3.84 g. 0.060 mol) in 150 ml of freshly distilled by THF at ice bath temperature. After the addition, the ice bath was removed and the reaction was allowed to proceed at 25° C. for 43 hours. The solids that formed was filtered to yield 8.48 g of waxy solid residue. The residue was ground to a fine powder and stirred in 150 ml of distilled water at ice bath temperature. The resulting soapy suspension (pH 11) was acidified to pH 2 with 10% HCl, then filtered and air-dried to give 5.4 g (96.3% yield) of crude 6 as a white solid. This was dissolved in warm THF and the mixture filtered. The filtrate was concentrated in vacuo until the solution became slightly turbid. This material was crystallized from THF/petroleum ether to yield 3.6 g (crop 1) of white powder. The filtrate was concentrated and crystallized in the same fashion to yield additional 0.6 g (crop 2) of white powder (74.8% total yield), mp 62°-65° C. TLC: Rf =0.68 in ethyl acetate/petroleum ether/glacial acetic acid (10:20:1); IR (Nujol, cm-1) 3230 (NH), 2250 (C≡N), 1740 (C=O); NMR (Silanor C, δ from TMS (1.3-1.6 (t, --CH2 --CH2 --C=O), 1-1.8 L (m, --(CH2)13 --), 0.8-1 (t, CH3 --CH2 --); Anal. Calcd for C17H32N2O: C, 72.81; H, 11.50; N, 9.99. Found: C, 72.69; H, 11.65; N, 9.68.

후처리

  1. additionwas added drop-wise
  2. distillationof freshly distilled by THF at ice bath temperature
  3. additionAfter the addition
  4. customthe ice bath was removed
  5. customThe solids that formed
  6. filtrationwas filtered
  7. customto yield 8.48 g of waxy solid residue
  8. filtrationfiltered
  9. customair-dried

출처 및 근거

ORD 기록
ord-9e9b84415c51468ca424d6f33c7ee4f0
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04870056

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