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

HRID 23393Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 140 °C

Procedure

(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.

Workup

customplaced in an oil bath

Sources & evidence

ORD record: ord-ed60cabcf70c4747a40da551dea5e2cb
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852726B2

Reaction notes

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