Phenylacetaldehyde → Dimethyl[2-(prop-2-yn-1-yloxy)ethyl]amine

HRID 871063

반응식

HRID 871063 반응식
[C:1]1([CH2:7][CH:8]=[O:9])C=CC=CC=1.[N+]([C:13]1C=CC=C[C:14]=1CC=O)([O-])=O.NN[C:24]([NH2:26])=S.[C-:27]#N.[Na+].[NH4+].[Cl-]>O.CO>[CH3:27][N:26]([CH3:24])[CH2:13][CH2:14][O:9][CH2:8][C:7]#[CH:1]

참가 물질

7

반응물 5

HCID 998PhenylacetaldehydeHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 2723789ThiosemicarbazideHCID 108447642-Nitrobenzeneacetaldehyde

생성물 1

HCID 12336591Dimethyl[2-(prop-2-yn-1-yloxy)ethyl]amine수율 10%

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

반응 조건

온도
50 °C

실험 절차

To a solution of the phenyl-acetaldehyde 1a or 2-nitro-phenyl-acetaldehyde 1b (8.3 mmol), thiosemicarbazide 2b (0.757 gr, 8.32 mmol) in H2O-methanol 55 ml (1:10 v/v) were added NaCN (0.624 g, 12.7 mmol) and NH4Cl (1.04 g, 19.44 mmol). The reaction mixture was stirred overnight at 50° C. The product from 1b was filtered, washed with cold water and dried under vacuum yielding 0.157 g (10%) of pure hydrazinecarbothioamide (3b). The precipitated crude product from 1a was purified on C18-reversed phase flash chromatography column employing a linear gradient of 0-30% A in B (flow-rate 40 mL/min), where A is 0.1% formic acid in CH3CN and B is 0.1% of formic acid in water, yielding 310 mg (15%) of pure 3b.

후처리

  1. filtrationThe product from 1b was filtered
  2. washwashed with cold water
  3. customdried under vacuum

출처 및 근거

ORD 기록
ord-fa033966e32d4968a836450545a428d2
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969573B2

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