Formaldehyde → 4-bis(phenylmethyl)amino-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-2-methanol

HRID 374986

반응식

HRID 374986 반응식
C([Li])CCC.[C:6](=[O:8])=O.CC(C)=O.[C:13]1([CH2:19][N:20]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:21]2[C:30]3[N:31]=[CH:32][N:33]([CH2:34][O:35][CH2:36][CH3:37])[C:29]=3[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)=O.C(Cl)(Cl)(Cl)Cl.C=O>O1CCCC1>[C:39]1([CH2:38][N:20]([CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:21]2[C:30]3[N:31]=[C:32]([CH2:6][OH:8])[N:33]([CH2:34][O:35][CH2:36][CH3:37])[C:29]=3[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=2)[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

참가 물질

7

반응물 5

HCID 712FormaldehydeHCID 18522661Acetone cardiceHCID 18995666N,N-bis(phenylmethyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amineHCID 86602444Carbontetrachloride dry-iceHCID 178418339Butyllithium

생성물 1

HCID 189956654-bis(phenylmethyl)amino-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-2-methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Butyllithium (1.6 mL of 2.5M in hexanes, 4 mmole) was added to a chilled (dry ice/acetone bath) solution of N,N-bis(phenylmethyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (1.7 g, 4 mmole) in tetrahydrofuran. No color change was observed. The reaction mixture was warmed to -20° C. (dry ice/carbon tetrachloride) and the reaction turned red in color. Formaldehyde gas entrained in a flow of nitrogen was added to the reaction mixture. After several minutes the reaction turned to a solid mass and the ice bath was removed. The reaction mixture was allowed to warm to ambient temperature and the color of the reaction mixture changed from red to yellow. The reaction was diluted with diethyl ether and water. The ether layer was separated, dried over magnesium sulfate and then concentrated under vacuum. The residue was purified by column chromatography (silica gel eluting with 10-20% ethyl acetate in hexanes v/v) to provide 1 g of 4-bis(phenylmethyl)amino-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-2-methanol.

후처리

  1. additionwas added to the reaction mixture
  2. waitAfter several minutes the reaction turned to a solid mass
  3. customthe ice bath was removed
  4. additionThe reaction was diluted with diethyl ether and water
  5. customThe ether layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by column chromatography (silica gel eluting with 10-20% ethyl acetate in hexanes v/v)

출처 및 근거

ORD 기록
ord-db242ccd6c31490594b3cf4e65d94c64
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05482936

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