Acetonitrile → 1-(6-(2-Cyanoacetyl)-2-benzothiazolyl)-3-ethylurea

HRID 9137Notes

Reaction equation

C(O[C:4]([C:6]1[CH:20]=[CH:19][C:9]2[N:10]=[C:11]([NH:13][C:14]([NH:16][CH2:17][CH3:18])=[O:15])[S:12][C:8]=2[CH:7]=1)=[O:5])C.[C:21](#[N:23])[CH3:22].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1>CN(C=O)C>[C:21]([CH2:22][C:4]([C:6]1[CH:20]=[CH:19][C:9]2[N:10]=[C:11]([NH:13][C:14]([NH:16][CH2:17][CH3:18])=[O:15])[S:12][C:8]=2[CH:7]=1)=[O:5])#[N:23]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-(6-ethoxycarbonyl-2-benzothiazolyl)-3-ethylurea (1.20 g, 4.09 mmol) in 5 mL of anhydrous DMF was treated with 2 mL of acetonitrile, cooled down to about 0° C., followed by treatment with 1 M LiHMDS in THF (13.1 mL, 13.1 mmol, 3.2 eq). It was stirred at the temperature for about 0.5 hour, then warmed up to room temperature, and stirred for another 4 hours. More LiHMDS (4 mL, 4.0 mmol, 1.0 eq) was added after the first hour. The mixture was quenched with MeOH and water, concentrated, and purified by flash chromatography on SiO2 with MeOH and methylene chloride (1/50) to give the desired compound 0.640 g (54%). LC/MS 288.9 (M+1); LC retention time 2.56 min.

Workup

temperaturewarmed up to room temperature
stirringstirred for another 4 hours
customThe mixture was quenched with MeOH and water
concentrationconcentrated
custompurified by flash chromatography on SiO2 with MeOH and methylene chloride (1/50)

Sources & evidence

ORD record: ord-8549526be9da42f8b9e0ee50ad49b065
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Reaction notes

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