Triethylamine → HCID 9879695, compound

HRID 433648Notes

Reaction equation

C(N(CC)CC)C.[CH2:8]([O:10][C:11]1[CH:19]=[CH:18][C:17]([S:20]([N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)(=[O:22])=[O:21])=[CH:16][C:12]=1[C:13]([NH2:15])=O)[CH3:9].FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[CH2:8]([O:10][C:11]1[CH:19]=[CH:18][C:17]([S:20]([N:23]2[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]2)(=[O:22])=[O:21])=[CH:16][C:12]=1[C:13]#[N:15])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (49.1 g, 0.485 Mol) was added to a slurry of 2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)benzamide (40.9 g, 0.125 Mol) in dichloromethane (200 mL) and this mixture was cooled to 0° C. Trifluoroacetic anhydride (58.9 g, 0.28 Mol) was added dropwise over 45 min and was washed in with DCM (25 mL) before the reaction was stirred at ambient temperature for 18 h. Water (125 mL) was added to the reaction with cooling. The layers were separated and the organic phase was washed with water before evaporation. The residue was stirred with ethyl acetate (150 mL) giving a crystalline solid which was filtered off and dried under vacuum; 27.4 g, 71%. m.p.=130-131° C. M/Z=310 (M+H); 1H NMR (300 MHz, CDCl3): 1.55 (t, 3H), 2.30 (s, 3H), 2,50 (m, 4H), 3.06 (m, 4H), 4.26 (quart. 2H), 7.08 (d, 1H), 7.90 (dd, 1H), 7.97 (d, 1H)

Workup

washwas washed in with DCM (25 mL) before the reaction
additionWater (125 mL) was added to the reaction
temperaturewith cooling
customThe layers were separated
washthe organic phase was washed with water before evaporation
stirringThe residue was stirred with ethyl acetate (150 mL)
customgiving a crystalline solid which
filtrationwas filtered off
customdried under vacuum

Sources & evidence

ORD record: ord-ff5f5d0ed78148ac95068842e7798091
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06667398B2

Reaction notes

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