1-Chloroethyl acetate → HCID 13506650, compound

HRID 1583300Notes

Reaction equation

[CH3:1][N:2]1[S:11](=[O:13])(=[O:12])[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]([OH:14])=[C:3]1[C:15]([NH:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][N:23]=1)=[O:16].[C:24]([O:27][CH:28](Cl)[CH3:29])(=[O:26])[CH3:25]>>[C:24]([O:27][CH:28]([O:14][C:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[S:11](=[O:13])(=[O:12])[N:2]([CH3:1])[C:3]=1[C:15]([NH:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][N:23]=1)=[O:16])[CH3:29])(=[O:26])[CH3:25]

Participants

Reactant 2

HCID 5218651-Chloroethyl acetate

HCID 54676228Piroxicam

Product 1

HCID 13506650HCID 13506650, compound

Procedure

By the procedure of Example 5, piroxicam (2.00 g, 6.0 mmol) and alpha-chloroethyl acetate (2.22 g, 18.1 mmol) were converted to chromatographed title product, 1.17 g of yellow solid (2.8 mmol, 46.4%) which gave white crystals (1.08 g) upon crystallization from isopropyl alcohol: mp 161°-162° C.; IR (KBr) 1755, 1677 cm-1 ; 1H NMR (CDCl3) delta 1.72 (d, J=6 Hz, 3H), 1.95 (s, 3H), 3.13 (s, 3H), 6.39 (q, J=6 Hz, 1H), 7.07-7.18 (m, 1H), 7.65-7.96 (m, 5H), 8.30-8.42 (m, 2H), 9.52 (br s, 1H); precise mass calcd for C17H15N3O5S m/e (P+ --C2H4O) 373.0738, found 373.0678.

Sources & evidence

ORD record: ord-7d56d5e80d2e4cb589ffe04c21c950bf
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04551452

Reaction notes

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