Triethylamine → 1-(7-Trimethylsilylacetylenyl-2-benzothiazolyl)-3-ethylurea

HRID 9120Notes

Reaction equation

FC(F)(F)S([C:6]1[C:14]2[S:13][C:12]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[N:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)(=O)=O.C(N(CC)CC)C.[CH3:30][Si:31]([C:34]#[CH:35])([CH3:33])[CH3:32]>CN(C=O)C.CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:30][Si:31]([C:34]#[C:35][C:6]1[C:14]2[S:13][C:12]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[N:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea (0.080 g, 80% pure, 0.17 mmol), Pd(PPh3)2Cl2 (0.010 g, 0.014 mmol, 0.08 eq), and triethylamine (0.102 mL, 0.73 mmol, 4.3 eq) in 1 mL of anhydrous DMF was bubbled with nitrogen gas for 5 minutes, followed by the addition of trimethylsilyl acetylene (0.12 mL, 0.85 mmol, 5.0 eq). The mixture was heated at about 100° C. with stirring in a sealed tube for about 18 hours. The mixture was cooled down, taken up in 10 mL MeOH, and evaporated to dryness. Purification by flash chromatography on SiO2 with ethyl acetate and heptane (2/1) gave pure desired compound 0.050 g (93%). LC/MS 318 (M+1); LC retention time 9.25 min.

Workup

customwas bubbled with nitrogen gas for 5 minutes
temperatureThe mixture was cooled down
customevaporated to dryness
customPurification by flash chromatography on SiO2 with ethyl acetate and heptane (2/1)

Sources & evidence

ORD record: ord-1a6875afea914c3fb284eeb3add847f4
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Reaction notes

Loading…