HCID 86700137, compound → HCID 86700138, compound

HRID 879339Notes

Reaction equation

[Br:1][C:2]1[S:3][C:4]2[C:10]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)(O)/[C:9](=[CH:19]/[C:20]([O:22][CH2:23][CH3:24])=[O:21])/[CH:8]([CH3:25])[CH2:7][C:5]=2[N:6]=1>C1COCC1>[Br:1][C:2]1[S:3][C:4]2[C:10]([C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)=[C:9]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:8]([CH3:25])=[CH:7][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Polyphosphoric acid (PPA) (140 g) and THF (210 mL) were heated to 75° C. in a 1 L recovery flask. (E)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-7-hydroxy-5-methyl-4,5-dihydrobenzo[d]thiazol-6(7H)-ylidene)acetate (31.0 g, 70.0 mmol) was added via addition funnel in THF (70 mL) over 2 min. The funnel was rinsed with THF (20 mL). The reaction mixture was heated at 80° C. for 2.5 h. After cooling to rt, the mixture was poured onto a 1 M K2HPO4 (1.5 L) solution followed by EtOAc (700 mL). The layers were separated, and the organic layer was washed with brine (500 mL). The organic layer was dried, filtered, and concentrated in vacuo to give desired product that was used without further purification. 1H NMR (400 MHz, CDCl3): δ 7.81 (s, 1H), 7.45 (d, 2H, J=8 Hz), 7.29 (d, 2H, J=8 Hz), 4.13 (q, 2H, J=7 Hz), 3.57 (s, 2H), 2.45 (s, 3H), 1.23 (t, 3H, J=7 Hz).

Workup

washThe funnel was rinsed with THF (20 mL)
temperatureAfter cooling to rt
additionthe mixture was poured onto a 1 M K2HPO4 (1.5 L) solution
customThe layers were separated
washthe organic layer was washed with brine (500 mL)
customThe organic layer was dried
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d2a4a3dbe9bb4c15acb69627f7908ce1
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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