Ethyl propiolate → HCID 6625404, compound

HRID 1465177Notes

Reaction equation

HRID 1465177 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]SNC1C=CC=CC=1.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[C:18]#[CH:19]>C(OCC)(=O)C.CCCCCC>[S:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][CH:19]=[C:18]1[C:17]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 85942866HCID 85942866, compound

Product 1

HCID 6625404HCID 6625404, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
150 °C

Procedure

2-(2-Aminophenyl)disulfanylaniline (1.0 g, 4.0 mmol) and ethyl prop-2-ynoate (790 mg, 816 μL, 8.05 mmol) were combined in a microwave tube and heated at 150° C. for 30 min. The reaction was concentrated in vacuo. Silica gel chromatography (10-35% ethyl acetate/hexane) provided ethyl 4H-1,4-benzothiazine-2-carboxylate as an orange solid (200 mg, 23% yield). LC/MS m/z 222.0 [M+H]+. 1H NMR (400.0 MHz, CDCl3) δ 7.11 (d, J=6.6 Hz, 1H), 6.86-6.82 (m, 1H), 6.79-6.74 (m, 2H), 6.27 (d, J=7.9 Hz, 1H), 5.68 (br d, J=4.2 Hz, 1H), 4.19 (q, J=7.2 Hz, 2H), 1.28 (t, J=7.1 Hz, 3H)

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-c50b1f68a67f49abb1b198b7b8294fd3
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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