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2,4-Dichlorobenzoyl chloride → 2,4-Dichloro-N-[(8-cyclopropylmethyl-1,4-dioxaspiro[4.5]dec-8-yl)methyl]benzamide

HRID 2263601
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HRID 2263601 반응식
[CH:1]1([CH2:4][C:5]2([CH2:15][NH2:16])[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30]>C(Cl)Cl>[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:28]=1[C:29]([NH:16][CH2:15][C:5]1([CH2:4][CH:1]2[CH2:3][CH2:2]2)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1)=[O:30]
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참가 물질

5

반응물 3

HCID 666452,4-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 686836208-(Cyclopropylmethyl)-1,4-dioxaspiro[4.5]decane-8-methanamine

생성물 1

HCID 686824732,4-Dichloro-N-[(8-cyclopropylmethyl-1,4-dioxaspiro[4.5]dec-8-yl)methyl]benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of {[8-(cyclopropylmethyl)-1,4-dioxaspiro[4.5]dec-8-yl]methyl}amine (7 g; 31.0 mmol) and n-ethyldiisopropylamine (6.45 ml; 37.2 mmol) in DCM (60 ml) at 0° C. was added 2,4-dichlorobenzoyl chloride (4.781 ml; 34.17 mmol) dropwise and the solution stirred for 4 hours warming to ambient temperature. The reaction was partitioned between DCM (50 ml) and water (20 ml). The aqueous phase was extracted with DCM (20 ml) and the combined organics dried over MgSO4, filtered and evaporated to give a colourless oil which was used in the next step without further purification. (11.5 g) 1H NMR δ (ppm) (CDCl3): 7.67 (1H, d, J=8.3 Hz), 7.43 (1H, d, J=2.0 Hz), 7.32 (1H, dd, J=2.0, 8.4 Hz), 6.25 (1H, s), 3.93 (4H, s), 3.56 (2H, d, J=6.2 Hz), 1.67 (8H, m), 1.33 (2H, d, J=6.7 Hz), 0.75-0.65 (1H, m), 0.51-0.47 (2H, m), 0.05 (2H, q, J=5.0 Hz). MS (m/e)=398

후처리

  1. customThe reaction was partitioned between DCM (50 ml) and water (20 ml)
  2. extractionThe aqueous phase was extracted with DCM (20 ml)
  3. dry with materialthe combined organics dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a colourless oil which
  7. customwas used in the next step without further purification

출처 및 근거

ORD 기록
ord-76d2f20d829446f187db4238929bcd4e
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07851638B2

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