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Triethylamine → 6-Chloro-9-(2-benzoyloxyethoxymethyl)purine

HRID 848075
ノート
印刷プレビュー

反応式

HRID 848075 の反応式
[C:1]([O:9][CH2:10][CH2:11][O:12][CH2:13]Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]2[C:17]=1[NH:18][CH:19]=[N:20]2.C(N(CC)CC)C.Cl.C(N(CC)CC)C>CN(C)C=O>[Cl:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]2[C:17]=1[N:18]=[CH:19][N:20]2[CH2:13][O:12][CH2:11][CH2:10][O:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 27245002-(Chloromethoxy)ethyl benzoateHCID 53592776-Chloropurine

生成物 1

HCID 129267736-Chloro-9-(2-benzoyloxyethoxymethyl)purine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Following substantially the procedure of Schaeffer, et al. supra but with minor modifications, 1-benzoyloxy-2-chloromethoxyethane (4.4 g) was added with stirring to a dry solution of 6-chloropurine (3.1 g) and triethylamine (6.5 ml) in dimethylformamide (50 ml). The reaction was exothermic, immediately precipitating triethylamine hydrochloride. The reaction mixture was stirred at room temperature for 24 hours and filtered. The filtrate was evaporated on a rotary evaporator at 70° C. The remaining thick amber oil was dissolved in the minimum amount of benzene and purified by column chromatography using a silica gel column. Benzene elution removed a trace of an unidentified material. Elution with ether first removed a small amount of ethylene glycol monobenzoatc and then 6-chloro-9-(2-benzoyloxyethoxymethyl)purine. Recrystallization from ether gave a white material, m.p. 108.5°-111° C.

後処理

  1. filtrationfiltered
  2. customThe filtrate was evaporated on a rotary evaporator at 70° C
  3. dissolutionThe remaining thick amber oil was dissolved in the minimum amount of benzene
  4. custompurified by column chromatography
  5. washBenzene elution
  6. customremoved a trace of an unidentified material
  7. washElution with ether
  8. customfirst removed a small amount of ethylene glycol monobenzoatc
  9. customRecrystallization from ether
  10. customgave a white material, m.p. 108.5°-111° C.

出典と根拠

ORDレコード
ord-c6a8d08acf894e27b41c5452f7069c82
出典データセット
uspto-grants-1981_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04294831

反応ノート

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