Ethylenediamine → 7-Chloro-1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-3-methanesulfonyl-1H-indole

HRID 23393ノート

反応式

HRID 23393 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]#[N:13])[CH:8]=[C:7]2[S:14]([CH3:17])(=[O:16])=[O:15].[CH2:18](N)[CH2:19][NH2:20]>C(=S)=S>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]1[NH:20][CH2:19][CH2:18][N:13]=1)[CH:8]=[C:7]2[S:14]([CH3:17])(=[O:16])=[O:15]

参加物

4

反応物 2

HCID 3301EthylenediamineHCID 22574041(7-Chloro-3-methanesulfonyl-indol-1-yl)-acetonitrile

生成物 1

HCID 101256517-Chloro-1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-3-methanesulfonyl-1H-indole

試薬・触媒・溶媒 1

HCID 6348Carbon Disulfide触媒

反応条件

温度
140 °C

実験手順

(7-chloro-3-methanesulfonyl-indol-1-yl)-acetonitrile (2.1 g) from Step 7 was dissolved in ethylene diamine (10 ml) and 2 drops of carbon disulfide were added. The flask was blanketed with nitrogen and then placed in an oil bath previously heated to 140° C. The mixture was stirred and after 30 minutes checked by mass spec which revealed the complete absence of starting material and the appearance of the desired product (positive ion spectrum) as well as an undetermined amount of unalkylated impurity from the previous reaction (negative ion spectrum). After 45 minutes, the reaction was cooled to room temperature and then placed in an ice bath. The product crystallized. Ethyl acetate (10 ml) was added and the precipitate was broken up, filtered, and then washed with a bit of ethyl acetate followed by ether. Air drying gave 1.22 g of a colorless crystalline solid, 7-chloro-1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-3-methanesulfonyl-1H-indole which after vacuum drying overnight at 60° C. weighed 1.21 g. The material was analytically pure.

後処理

  1. customplaced in an oil bath

出典と根拠

ORDレコード
ord-ed60cabcf70c4747a40da551dea5e2cb
出典データセット
uspto-grants-2005_02
特許番号
US06852726B2

反応ノート

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