Triethylamine → HCID 131732576, compound

HRID 874684Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[C:16]2[CH:17]=[CH:18][C:19]([NH:21][CH:22]=O)=[CH:20][C:15]=2[O:14][N:13]=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.CCN(CC)CC>C(Cl)Cl>[N+:21]([C:19]1[CH:18]=[CH:17][C:16]2[C:12]([N:3]3[C:4](=[O:11])[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:2]3=[O:1])=[N:13][O:14][C:15]=2[CH:20]=1)#[C-:22]

Participants

Conditions

Temperature: 0 °C

Procedure

1-5 (150 mg, 0.480 mmol) was suspended in CH2Cl2 (10 mL) and cooled to 0° C. To the mixture were added triphosgene (87.0 mg, 0.290 mmol) followed by Et3N (0.140 mL, 0.980 mmol). The mixture was stirred at room temperature for 2 h. The mixture was diluted with CH2Cl2, washed with saturated aqueous NaHCO3, brine and dried over Na2SO4. The residue was triturated with hexane to give 115 mg (82%) of 1-6 as a pale yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 8.34 (1H, br s), 8.09 (2H, m), 8.04 (1H, dd, J=8.4, 0.8 Hz), 8.00 (2H, m), 7.68 (1H, dd, J=8.4, 1.6 Hz); ESI-MS m/z 290 [C16H7N3O3]+.

Workup

washwashed with saturated aqueous NaHCO3, brine
dry with materialdried over Na2SO4
customThe residue was triturated with hexane

Sources & evidence

ORD record: ord-f2a9e94229d3485ba4a4cdf789515019
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980916B2

Reaction notes

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