HCID 20260332, compound → HCID 13506652, compound

HRID 1583302Notes

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].Cl[CH:25]([O:27][C:28]([CH:30]1[CH2:32][CH2:31]1)=[O:29])[CH3:26]>>[CH:30]1([C:28]([O:27][CH:25]([O:14][C:4]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[S:11](=[O:13])(=[O:12])[N:2]([CH3:1])[C:3]=2[C:15]([NH:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][N:23]=2)=[O:16])[CH3:26])=[O:29])[CH2:32][CH2:31]1

Participants

Reactant 2

HCID 20260332HCID 20260332, compound

HCID 54676228Piroxicam

Product 1

HCID 13506652HCID 13506652, compound

Procedure

By the procedure of Example 6, piroxicam (3.00 g, 9.1 mmol) and cyclopropanecarboxylic acid alpha-chloroethyl ester (4.03 g, 27.2 mmol) were converted to title product, 3.51 g white foam (7.0 mmol, 87.3%) which gave 1.90 g white crystals from toluene; mp 176°-177° C.; IR (KBr) 1735, 1680 cm-1 ; 1H NMR (CDCl3) delta 0.70-0.97 (m, 4H), 1.37-1.50 (m, 1H), 1.72 (d, J=6 Hz, 3H), 3.11 (s, 3H), 6.40 (q, J=6 Hz, 1H), 7.07-7.17 (m, 1H), 7.63.7.97 (m, 5H), 8.29-8.42 (m, 2H), 9.54 (br s, 1H); precise mass calcd for C21H22N3O6S m/e (P+ +H) 444.1235, found 444.1013.

Sources & evidence

ORD record: ord-a000ecf41c5b4e41b140ec25f992de89
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04551452

Reaction notes

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