1-Methylimidazole → n-Hexyl p-nitrophenyl phosphorochloridate

HRID 1368007ノート

反応式

HRID 1368007 の反応式
[P:1]([Cl:14])(Cl)(=[O:12])[O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[CH2:15]([OH:31])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]CCCCCCCCCC.CN1C=CN=C1>ClCCl.CCCCCC>[P:1]([Cl:14])(=[O:12])([O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)[O:31][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

参加物

6

反応物 3

HCID 13901-MethylimidazoleHCID 2682Cetyl AlcoholHCID 69898Phosphorodichloridic acid, 4-nitrophenyl ester

生成物 1

HCID 22501465n-Hexyl p-nitrophenyl phosphorochloridate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8058Hexane溶媒

実験手順

p-Nitrophenyl phosphorodichloridate (75 g, 0.29 mol) in anhydrous dichloromethane (300 mL) was added to a 1 L, three necked, round-bottomed flask with stir bar that had been purged with N2. A solution of hexadecanol (71.03 g, 0.29 mol) and N-methylimidazole (23.35 mL, 0.29 mol) in anhydrous dichloromethane (250 mL) was added dropwise over a period of 2 hours. The reaction mixture was stirred for an additional 1 hour before pouring into a 1 L separatory funnel. N-methylimidazole hydrochloride salts separated at the bottom as an oil and were removed from the funnel. Dichloromethane was removed from the mixture at less than 30° C. under vacuum to give an amber oil which was taken up in hexane (400 mL) and placed in a freezer overnight. The reaction mixture was then thawed and the soluble portion was filtered to remove the crystals of p-nitrophenyl phosphorodichloridate. The solvent was removed from the filtrate via rotary evaporation at less than 35° C. to give n-hexyl p-nitrophenyl phosphorochloridate.

後処理

  1. customhad been purged with N2
  2. stirringThe reaction mixture was stirred for an additional 1 hour
  3. additionbefore pouring into a 1 L separatory funnel
  4. customN-methylimidazole hydrochloride salts separated at the bottom as an oil
  5. customwere removed from the funnel
  6. customDichloromethane was removed from the mixture at less than 30° C. under vacuum
  7. customto give an amber oil which
  8. filtrationthe soluble portion was filtered
  9. customto remove the crystals of p-nitrophenyl phosphorodichloridate
  10. customThe solvent was removed from the filtrate via rotary evaporation at less than 35° C.

出典と根拠

ORDレコード
ord-47d5c7ac64c44890acbc43a75c0890a8
出典データセット
uspto-grants-2003_06
特許番号
US06572850B1

反応ノート

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