Benzoyl chloride → N-Naphth-1-yl-N-propylthiourea

HRID 1418033

반응식

HRID 1418033 반응식
C(Cl)(=O)C1C=CC=CC=1.[S-:10][C:11]#[N:12].[NH4+].[C:14]1([NH:24][CH2:25][CH2:26][CH3:27])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>CC(C)=O>[C:14]1([N:24]([CH2:25][CH2:26][CH3:27])[C:11]([NH2:12])=[S:10])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 346980N-propylnaphthalen-1-amine

생성물 1

HCID 54008331N-Naphth-1-yl-N-propylthiourea수율 62.2%

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

3.9 g of benzoyl chloride and 2.1 g of ammonium thiocyanate are introduced into anhydrous acetone in a three-necked flask under argon and maintained between 0° and 5° C., the reaction mixture is left stirring for 15 minutes and then 3.9 g of N-naphth-1-yl-N-propylamine, dissolved in acetone, are added dropwise. The reaction mixture is then heated at reflux for 1 hour and evaporated to dryness and the residue is taken up in concentrated hydrochloric acid, heated at reflux for 3 hours and allowed to return to room temperature. The organic products are extracted with diethyl ether and then successively basification is carried out with 33% sodium hydroxide, extraction is carried out with ethyl acetate, the organic phase is evaporated to dryness and the residue is purified on a column of silica gel eluted with a 75/25 (v/v) hexane/ethyl acetate mixture, to obtain 3.2 g of white crystals melting at 170°-171° C. 1H NMR (CDCl3): 0.86 (t, J=7.3, 3H, --CH2 --CH3), 1.68 (m, 2H, --CH2 --CH3), 3.72 (m, 2H, --CH2 --CH2 --CH3), 5.58 (m, 2H, --NH2), 7.37 (d, J=7.3, 1H, H2), 7.23 (m, 2H, H3 and H8), 7.75-7.80 (m, 2H, H6 and H7), 7.85-7.95 (m, 2H, H4 and H5).

후처리

  1. temperaturemaintained between 0° and 5° C.
  2. waitthe reaction mixture is left
  3. additionare added dropwise
  4. temperatureThe reaction mixture is then heated
  5. temperatureat reflux for 1 hour
  6. customevaporated to dryness
  7. temperatureheated
  8. temperatureat reflux for 3 hours
  9. customto return to room temperature
  10. extractionThe organic products are extracted with diethyl ether
  11. extractionsuccessively basification is carried out with 33% sodium hydroxide, extraction
  12. customthe organic phase is evaporated to dryness
  13. customthe residue is purified on a column of silica gel
  14. washeluted with a 75/25 (v/v) hexane/ethyl acetate mixture

출처 및 근거

ORD 기록
ord-522b9fa2a51e41e581e954e3dce7d484
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05880135

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