Triethylamine → HCID 11171593, compound

HRID 1489004Notes

Reaction equation

[CH2:1]([NH:5][C:6]([N:8]1[CH:12]=[CH:11][NH:10][C:9]1=[S:13])=[O:7])[CH2:2][CH2:3][CH3:4].BrBr.C(N(CC)CC)C>ClCCl>[CH2:1]([N:5]1[C:6](=[O:7])[N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[S:13]1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To solution containing 1-(butylcarbamoyl)-1,3-dihydroimidazole-2-thione (4.73 g, 23.7 mmole) suspended in 15 mL of dichloromethane cooled to 0° C. under a nitrogen atmosphere, was added bromine (3.79 g, 23.7 mmole) dissolved in 15 mL of dichloromethane, in a dropwise manner. After the addition was complete, triethylamine (4.81 g, 47.5 mmole) dissolved in 15 mL dichloromethane was added such that the temperature of the reaction mixture never exceeded 0° C. The reaction mixture was maintained at 0° C. for an additional 2 h and then stirred for 16 h at room temperature. It was then diluted with 150 mL of dichloromethane and washed twice with water and once with a saturated sodium chloride solution. The organic layer was then dried over magnesium sulfate and evaporated to dryness to yield 4.30 g (92%) of 2-butylimidazo[1,2-d]-1,2,4-thiadiazole-3(2H)-one as an off-white powder: mp 142°-143° C.; 1H NMR (CDCl3) δ7.40 (d, 1H), 7.20 (d, 1H), 3.79 (t, 2H), 1.73 (m, 2H), 1.40 (m, 2H), 0.957 (t, 3H) ppm; IR (KBr) ν1702 cm-1.

Workup

additionAfter the addition
additionwas added such that the temperature of the reaction mixture never exceeded 0° C
temperatureThe reaction mixture was maintained at 0° C. for an additional 2 h
washwashed twice with water and once with a saturated sodium chloride solution
dry with materialThe organic layer was then dried over magnesium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-8b1846172f1f4549953929bac451d400
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05677302

Reaction notes

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