HCID 59683351, compound → Ethyl 4H-pyrrolo[2,3-d][1,3]thiazole-5-carboxylate

HRID 2206570Notes

Reaction equation

[N:1](/[C:4](=[CH:10]\[C:11]1[S:15][CH:14]=[N:13][CH:12]=1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>C1(C)C=CC=CC=1>[S:15]1[C:11]2[CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH:1][C:12]=2[N:13]=[CH:14]1

Participants

Conditions

Temperature: 120 °C

Procedure

(Z)-ethyl 2-azido-3-(thiazol-5-yl)acrylate (9 g, 40.18 mmol) was dissolved in anhydrous toluene (100 mL), and the resulting reaction was allowed to stir for 2 hours at 120° C. The reaction mixture was concentrated and purified by column chromatograph on silica gel eluted with (petrol ether/acetic ester 15:1→10:1→8:1) to give the title compound (5 g, 63.5%) as an yellow solid. LCMS (M+H+) m/z: calcd. 196.03. found 196.9.

Workup

customthe resulting reaction
concentrationThe reaction mixture was concentrated
custompurified by column chromatograph on silica gel
washeluted with (petrol ether/acetic ester 15:1→10:1→8:1)

Sources & evidence

ORD record: ord-a9e52c6fee71487a8c14af8a851a4fdc
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371331B2

Reaction notes

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