HCID 13506639, compound → HCID 13506663, compound

HRID 1583296Notes

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:40])([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[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:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

Reactant 2

HCID 13506639HCID 13506639, compound

HCID 54676228Piroxicam

Product 1

HCID 13506663HCID 13506663, compound

Procedure

By the procedure of Example 6, piroxicam (3.00 g, 9.1 mmol) and alpha-chloroethyl decyl carbonate (4.79 g, 18.1 mmol) were converted to chromatographed title product, 4.46 g white foam (8.0 mmol, 88.0%) which gave white crystals from isopropyl alcohol: mp 84°-86° C.: IR (KBr) 1764, 1679 cm-1 ; 1H NMR (CDCl3) delta 0.89 (t, J=7 Hz, 3H), 1.09-1.41 (m, 14H), 1.41-1.60 (br m, 2H), 1.75 (d, J=6 Hz, 3H), 3.11 (s, 3H), 4.00 (t, J=7 Hz, 2H), 6.36 (q, J=6 Hz, 1H), 7.07-7.17 (m, 1H), 7.63-7.96 (m, 5H), 8.30-8.40 (m, 2H), 9.40 (br s, 1H); precise mass calcd for C28H37N3O7S m/e 559.2352, found 559.2346.

Sources & evidence

ORD record: ord-4d130af3571f4368993c81c0c872ef3e
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04551452

Reaction notes

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