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Hydrochloric Acid → 7-(2-methyl-1H-benzimidazol-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine dihydrochloride

HRID 241086
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HRID 241086 반응식
CC(OC([N:8]1[C:12]2[CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]4[O:26][CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][C:21]=4[CH:34]=3)[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH3:35])=O)(C)C.C(OCC)C.[ClH:41]>CO.O1CCOCC1>[ClH:41].[ClH:41].[CH3:35][C:9]1[NH:8][C:12]2[CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]4[O:26][CH2:25][CH2:24][NH:23][CH2:22][C:21]=4[CH:34]=3)[CH:15]=[CH:16][C:11]=2[N:10]=1
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 59604600tert-butyl 7-(1-(tert-butoxycarbonyl)-2-methyl-1H-benzo[d]imidazol-6-yl)-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate

생성물 1

HCID 668202277-(2-methyl-1H-benzimidazol-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine dihydrochloride수율 93%

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 312751,4-Dioxane용매

실험 절차

A solution of 1,1-dimethylethyl 7-(1-{[(1,1-dimethylethyl)oxy]carbonyl}-2-methyl-1H-benzimidazol-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (13.1 g, 27 mmol) in a mixture of methanol (20 mL) and 4 N hydrogen chloride in dioxane (30 mL) was refluxed for 15 min. After cooling to room temperature ethyl ether (100 mL) was added, and the reaction mixture was concentrated. Another portion of ethyl ether (100 mL) was added, the precipitate was filtered off, washed several times with ethyl ether, and dried to give 7-(2-methyl-1H-benzimidazol-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine dihydrochloride (8.9 g, 93% yield) as a light beige solid. 1HNMR (400 MHz, CD3OD): 7.93 (s, 1H), 7.86-7.67 (m, 4H), 7.28 (s, 1H), 4.54 (s, 2H), 4.33-4.23 (m, 2H), 3.65-3.54 (m, 2H), 2.91 (s, 3H); MS (EI) for C17H17N3O: 280 (MH+).

후처리

  1. temperaturewas refluxed for 15 min
  2. additionwas added
  3. concentrationthe reaction mixture was concentrated
  4. additionAnother portion of ethyl ether (100 mL) was added
  5. filtrationthe precipitate was filtered off
  6. washwashed several times with ethyl ether
  7. customdried

출처 및 근거

ORD 기록
ord-7f8a88a01cfe46a2b644120913e932af
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08648066B2

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