Benzene → 1-tert-butoxycarbonyloxy-6-chloro-1H-benzotriazole

HRID 596216노트

반응식

HRID 596216 반응식
[C:1](Cl)(Cl)=O.[OH:5][N:6]1[C:10]2[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1.Cl[C:17]([O:19]N1C2C=C(Cl)C=CC=2N=N1)=[O:18].[CH:30]1[CH:35]=[CH:34]C=CC=1>N1C=CC=CC=1.C(O)(C)(C)C>[C:35]([O:19][C:17]([O:5][N:6]1[C:10]2[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1)=[O:18])([CH3:34])([CH3:30])[CH3:1]

참가 물질

7

반응물 4

HCID 241Benzene3회HCID 6371PhosgeneHCID 2327116-Chloro-1-hydroxy-1H-benzotriazoleHCID 205679821-chlorocarbonyloxy-6-chloro-1H-benzotriazole

생성물 1

HCID 132928521-tert-butoxycarbonyloxy-6-chloro-1H-benzotriazole

시약·촉매·용매 2

HCID 1049Pyridine용매2회HCID 6386tert-Butanol용매

실험 절차

A solution of phosgene (5 g.) in benzene (23.5 ml.) was dropwise added under ice-cooling to a suspension of 1-hydroxy-6-chloro-1H-benzotriazole (8.5 g.) and pyridine (3.9 g.) in benzene (50 ml.), and the mixture was stirred for 30 minutes at the same temperature and allowed to stand overnight. To the resultant solution containing 1-chlorocarbonyloxy-6-chloro-1H-benzotriazole was dropwise added, over 20 minutes under ice-cooling, a solution of tert-butyl alcohol (3.7 g.) and pyridine (4.0 g.) in benzene (50 ml.). The resultant mixture was stirred for 2 hours at the same temperature and allowed to stand overnight. The reaction mixture was filtered, and the filtrate was concentrated. Ether and petroleum ether were added to the residue to pulverize the residue and obtained crystals were collected by filtration to give 1-tert-butoxycarbonyloxy-6-chloro-1H-benzotriazole (5.3 g.). The mother liquor was concentrated to give the same object compound (0.6 g.). Both crystals were put together and dissolved in benzene, after which the solution was washed with a sodium bicarbonate aqueous solution and water and then dried. The solvent was removed by distillation to give the object compound (3.2 g.), powder, mp 98° to 100° C (dec.).

후처리

  1. waitto stand overnight
  2. additionwas dropwise added, over 20 minutes under ice-
  3. temperaturecooling
  4. waitto stand overnight
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated
  7. additionEther and petroleum ether were added to the residue
  8. customobtained crystals
  9. filtrationwere collected by filtration

출처 및 근거

ORD 기록
ord-1869df57661f4238a3d6a58ae4e3e5fe
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04010178

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