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

HRID 2082984ノート

反応式

HRID 2082984 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 added dropwise 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.). The mixture was stirred for 30 minutes at the same temperature and allowed to stand overnight. A solution of tert-butyl alcohol (3.7 g.) and pyridine (4.0 g.) in benzene (50 ml.) was added dropwise for 20 minutes under ice-cooling to the resultant solution containing 1-chlorocarbonyloxy-6-chloro-1H-benzotriazole. 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 the resultant 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 desired compound (0.6 g.). Both quantities of crystals were mixed together and dissolved in benzene. The resultant solution was then washed with a sodium bicarbonate aqueous solution and water and then dried. The solvent was removed by distillation to give the desired compound (3.2 g.), powder, mp 98° to 100° C (dec.).

後処理

  1. waitto stand overnight
  2. waitto stand overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. additionEther and petroleum ether were added to the residue
  6. filtrationthe resultant crystals were collected by filtration

出典と根拠

ORDレコード
ord-b685f89cc4d14a918731e2411fed372b
出典データセット
uspto-grants-1978_04
特許番号
US04083848

反応ノート

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