1,1'-Carbonyldiimidazole → HCID 87463850, compound

HRID 1260356Notes

Reaction equation

[F:1][C:2]1([F:18])[O:6][C:5]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:15][C:14](=[CH2:16])[S:13][C:12]3=[NH:17])=[CH:10][C:4]=2[O:3]1.[C:19](N1C=CN=C1)([N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)=[O:20]>C(#N)C.C(Cl)Cl>[F:18][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:15][C:14](=[CH2:16])[S:13]/[C:12]/3=[N:17]\[C:19]([N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)=[O:20])=[CH:10][C:4]=2[O:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-5-methylenethiazolidin-2-imine (Example 115, 0.2 g, 0.74 mmol) and carbonyldiimidazole (0.14 g, 0.92 mmol) in dry acetonitrile (5 mL) was stirred at 70° C. for 16 hours. After cooling down, the mixture was diluted with 150 mL of CH2Cl2 and washed successively with saturated sodium bicarbonate (75 mL), water (75 mL) and brine (75 mL). The organic phase was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was chromatographed over silica using 100% CH2Cl2 to CH2Cl2:MeOH 95:5 as mobile phase to give the titled compound. 1H NMR (CD3OD) δ ppm 5.00 (2H), 5.40 (1H), 5.50 (1H), 6.90 (1H), 7.35 (2H), 7.44 (1H), 7.50 (1H), 8.05 (1H); MS (ESI) m/z 365(M+H)+.

Workup

temperatureAfter cooling down
washwashed successively with saturated sodium bicarbonate (75 mL), water (75 mL) and brine (75 mL)
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
customevaporated under reduced pressure
customThe residue was chromatographed over silica using 100% CH2Cl2 to CH2Cl2:MeOH 95:5 as mobile phase

Sources & evidence

ORD record: ord-3991c980ebee4aeda55aba90cdb817a2
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470813B2

Reaction notes

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