Bis(trimethylsilyl)carbodiimide → N-(5'-(3-cyanophenyl)-5,7,8,9-tetrahydrospiro[benzo[7]annulene-6,2'-indene]-3'(1'H)-ylidene)cyanamide

HRID 1503396노트

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HRID 1503396 반응식
O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])[CH:9]=2)[CH2:4][C:3]21[CH2:24][CH2:23][CH2:22][C:21]1[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=1[CH2:19]2.C[Si]([N:33]=[C:34]=[N:35][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:14]([C:13]1[CH:12]=[C:11]([C:8]2[CH:7]=[C:6]3[C:5](=[CH:10][CH:9]=2)[CH2:4][C:3]2([CH2:19][CH2:20][CH2:28][C:27]4[CH:23]=[CH:22][CH:21]=[CH:25][C:26]=4[CH2:2]2)[C:24]3=[N:35][C:34]#[N:33])[CH:18]=[CH:17][CH:16]=1)#[N:15]

참가 물질

5

반응물 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 670437003-(1'-Oxo-1',3',5,7,8,9-hexahydrospiro[benzo[7]annulene-6,2'-indene]-6'-yl)benzonitrile

생성물 1

HCID 86652171N-(5'-(3-cyanophenyl)-5,7,8,9-tetrahydrospiro[benzo[7]annulene-6,2'-indene]-3'(1'H)-ylidene)cyanamide수율 150%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

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온도
50 °C

실험 절차

To a solution of 3-(1′-oxo-1′,3′,5,7,8,9-hexahydrospiro[benzo[7]annulene-6,2′-indene]-6′-yl)benzonitrile (31 mg, 0.086 mmol) in CH2Cl2 (2 mL) was added TiCl4 (66 mg). It was stirred in microwave at 50° C. for 5 minutes. Then bis-trimethylsilylcarbodiimide (112 mg, 0.6 mmol) was added. The resulting mixture was stirred in microwave at 60° C. for 10 minutes. The reaction mixture was poured into ice-water, extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to give N-(5′-(3-cyanophenyl)-5,7,8,9-tetrahydrospiro[benzo[7]annulene-6,2′-indene]-3′(1′H)-ylidene)cyanamide (50 mg, crude).

후처리

  1. stirringThe resulting mixture was stirred in microwave at 60° C. for 10 minutes
  2. extractionextracted with DCM
  3. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-933841b778d94d7597ceb442e556884e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212153B2

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