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Chlorotrimethylsilane → 1-(Triphenylmethyl)-1H-imidazole-4-propanoic acid

HRID 1167445
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HRID 1167445 반응식
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[N:3]=[CH:2]1.C[Si](Cl)(C)C.C(N(CC)CC)C.Cl[C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl.C(#N)C.CO>[C:25]1([C:24]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:1]2[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[N:3]=[CH:2]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 6456Trityl chlorideHCID 8471Triethylamine2회HCID 178525356HCID 178525356, 화합물

생성물 1

HCID 74084421-(Triphenylmethyl)-1H-imidazole-4-propanoic acid수율 82.9%

시약·촉매·용매 3

HCID 887Methanol
용매
HCID 6342Acetonitrile용매
HCID 6344Dichloromethane용매2회

실험 절차

3-(4-Imidazolyl)propionic acid (1.0 g, 7.1 mmol) was suspended in a mixture of dichloromethane (5 ml) and acetonitrile (25 ml). Trimethylsilyl chloride (781 mg, 7.2 nmmol) was added and the mixture refluxed for 4 hours. Triethylamine (1 ml) was added, and refluxing continued for 15 minutes. Cooled, triethylamine (1 ml) added followed by chlorotriphenylmethane (1.99 g, 7.1 mmol) in dichloromethane (10 ml), and the mixture stirred at ambient temperature for 2 hours. MeOH (20 ml) was added, the mixture stirred for 30 minutes, then evaporated to dryness. Water (50 ml) was added to the residue, and the pH adjusted to 8-8.5 with triethylamine. The precipitate was filtered off, washed with diethyl ether, and dried to give the desired product (2.25 g). MS (ESP): 383 (MH+) for C25H22N2O2;

후처리

  1. temperaturethe mixture refluxed for 4 hours
  2. temperaturerefluxing
  3. temperatureCooled
  4. stirringthe mixture stirred for 30 minutes
  5. customevaporated to dryness
  6. additionWater (50 ml) was added to the residue
  7. filtrationThe precipitate was filtered off
  8. washwashed with diethyl ether
  9. customdried

출처 및 근거

ORD 기록
ord-ad6a48cc776640f1baf8c40bbc12dd69
출처 데이터셋
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06617339B1

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