Acetic Anhydride → HCID 67263601, 화합물

HRID 1688016노트

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HRID 1688016 반응식
[C:1](OC(=O)C)(=[O:3])[CH3:2].[N+:8]([C:11]1[CH:12]=[CH:13][C:14]2[O:20][CH2:19][CH2:18][CH2:17][NH:16][C:15]=2[CH:21]=1)([O-:10])=[O:9].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(#N)C.CCOC(C)=O>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]2[O:20][CH2:19][CH2:18][CH2:17][N:16]([C:1](=[O:3])[CH3:2])[C:15]=2[CH:21]=1)([O-:10])=[O:9]

참가 물질

7

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 109871302,3,4,5-Tetrahydro-7-nitro-1,5-benzoxazepine

생성물 1

HCID 67263601HCID 67263601, 화합물수율 74%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

Acetic anhydride (1.00 mL, 10.6 mmol;) was added to a solution of 2-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (0.580 g, 2.99 mmol), 4-Dimethylaminopyridine (20 mg, 0.1 mmol; Acros) and Triethylamine (1.0 mL, 7.2 mmol) in Acetonitrile (10 mL; Acros). The reaction was stirred under an atmosphere of Nitrogen overnight. Conversion was moderate, so the mixture was heated at 50° C. for the weekend. The solution was conc. in vacuo, diluted with 25 mL EtOAc then washed with 1N HCl (10 mL), satd. sodium bicarbonate (10 mL) and brine (10 mL). After drying over sodium sulfate, the solution was conc. and the residue chromatographed (ISCO, 80 g SiO2, 0-65% EtOAc:Hex) to afford 1-(2-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone as light yellow solids (522 mg, 74%). Mixture of rotamers in 1H-NMR, resulting in very broad signals for the aliphatic methylenes. 13C-NMR (CDCl3): 169.8, 160.3, 142.7, 134.3, 124.8, 124.6, 122.6, 71.1, 45.0, 28.0, 22.4

후처리

  1. washthen washed with 1N HCl (10 mL)
  2. dry with materialAfter drying over sodium sulfate
  3. customthe residue chromatographed (ISCO, 80 g SiO2, 0-65% EtOAc:Hex)

출처 및 근거

ORD 기록
ord-b97659a403534ba1b17f898ec1aeac82
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148391B2

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