Trityl chloride → 5-phenyl-1-trityl-1H-tetrazole

HRID 538843

반응식

HRID 538843 반응식
[C:1]1([C:7]2[NH:11][N:10]=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:20]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:1]1([C:7]2[N:11]([C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:10]=[N:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418369HCID 178418369, 화합물

생성물 1

HCID 104303585-phenyl-1-trityl-1H-tetrazole수율 94.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 5-phenyl-1H-tetrazole (50.0 g, 342.1 mmol, 1.00 equiv) in DCM (dried) (150 mL) was placed in a flask that had been purged and maintained with an inert atmosphere of nitrogen. Triethylamine (45.0 g, 444.7 mmol, 1.30 equiv) at 0° C. was added to the mixture, followed by the addition of chlorotriphenylmethane (100.0 g, 358.7 mmol, 1.05 equiv) in several batches at 0° C. The resulting solution was stirred for 3 hours at room temperature. The solids were collected by filtration, and the filtrate cake was washed with cold EtOAc (1×100 mL) and water (3×300 mL). The solid was dried under reduced pressure to yield 125 g (94%) of 5-phenyl-1-trityl-1H-tetrazole as a white solid. ES m/z: [M+H]+ calcd for C26H20N4, 389.1. found 389.1.

후처리

  1. customthat had been purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. filtrationThe solids were collected by filtration
  4. washthe filtrate cake was washed with cold EtOAc (1×100 mL) and water (3×300 mL)
  5. customThe solid was dried under reduced pressure

출처 및 근거

ORD 기록
ord-1a49ea5e26c34a65b4f2c2e24f0c3a20
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865755B2

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