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

HRID 596216ノート

反応式

HRID 596216 の反応式
[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]

参加物

7

反応物 4

HCID 241Benzene3 回HCID 6371PhosgeneHCID 2327116-Chloro-1-hydroxy-1H-benzotriazoleHCID 205679821-chlorocarbonyloxy-6-chloro-1H-benzotriazole

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒2 回HCID 6386tert-Butanol溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-1869df57661f4238a3d6a58ae4e3e5fe
出典データセット
uspto-grants-1977_03
特許番号
US04010178

反応ノート

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