Formaldehyde → 1,4-Dibenzyl-6-benzyl-6-nitro-1,4-diazepane

HRID 424289

반응식

HRID 424289 반응식
[C:1](O)(=O)C.C(O)(=O)C.[CH2:9]([NH:16][CH2:17][CH2:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N+:27]([CH2:30][CH2:31]C1C=CC=CC=1)([O-:29])=[O:28].C=O.[C:40]1([CH3:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.CO>>[CH2:9]([N:16]1[CH2:31][C:30]([CH2:46][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([N+:27]([O-:29])=[O:28])[CH2:1][N:19]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:18][CH2:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

5

반응물 4

HCID 712Formaldehyde2회HCID 312281,2-Ethanediamine, N1,N2-bis(phenylmethyl)-, acetate (1:2)HCID 802081-Nitro-2-phenylethaneHCID 21867641Toluene methanol

생성물 1

HCID 585998471,4-Dibenzyl-6-benzyl-6-nitro-1,4-diazepane수율 89%

실험 절차

In a 250 mL round-bottom flask N,N′-dibenzylethylenediamine diacetate (19.67 g, 54.6 mmol) and 2-nitroethylbenzene (4, 8.28 g, 54.6 mmol) are dissolved in 1:1 toluene/methanol (100 mL). Paraformaldehyde (5.74 g, 0.191 mol) is added portion wise to the solution and the resulting suspension is refluxed. The mixture becomes homogeneous (dissolution of paraformaldehyde) and after 3 h at reflux, the mixture is cooled and evaporated in vacuo. The residue is recrystallized from methanol, obtaining pure 5 (20.29 g, 89%) as light yellow solid. M.p. 83-85° C. (EtOH), ESI-MS: 438 (MNa+), 416 (MH+); (Calc. for C26H29N3O2: 415 u.m.a.).

후처리

  1. temperaturethe resulting suspension is refluxed
  2. temperatureafter 3 h at reflux
  3. temperaturethe mixture is cooled
  4. customevaporated in vacuo
  5. customThe residue is recrystallized from methanol

출처 및 근거

ORD 기록
ord-613e51b5c25246efb9fbb35402fddf3f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08105567B2

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