91508-03-1 → HCID 13506668, compound

HRID 1583299Notes

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:34])([O:29][CH2:30][CH2:31][CH2:32][CH3:33])[O:25][CH:26](Cl)[CH3:27]>>[CH2:30]([O:29][C:24]([O:25][CH:26]([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])[CH3:27])=[O:34])[CH2:31][CH2:32][CH3:33]

Participants

Reactant 2

HCID 1350664291508-03-1

HCID 54676228Piroxicam

Product 1

HCID 13506668HCID 13506668, compound

Procedure

By the procedure of Example 6, piroxicam (3.00 g, 9.1 mmol) and alpha-chloroethyl butyl carbonate (5.30 g, 29.3 mmol) were converted to title product, 600 mg yellow solid (1.3 mmol, 13.9%) which was recrystallized from isopropyl alcohol to give 325 mg white crystals: mp 132°-133° C.; IR (KBr) 1758, 1681 cm-1 ; 1H NMR (CDCl3) delta 0.87 (t, J=7 Hz, 3H), 1.18-1.35 (m, 2H), 1.42-1.58 (m, 2H), 1.76 (d, J=6 Hz, 3H), 3.11 (s, 3H), 4.01 (t, J=7 Hz, 2H), 6.35 (q, J=6 Hz, 1H), 7.05-7.15 (m, 1H), 7.65-7.82 (m, 3H), 7.82-7.95 (m, 2H), 8.30-8.40 (m, 2H), 9.39 (br s, 1H): precise mass calcd for C22H25N3O7S m/e 475.1413, found 475,1425.

Sources & evidence

ORD record: ord-28c493f02e73449b8af71fe2e0ed4197
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04551452

Reaction notes

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