Carbonic acid, 1-chloroethyl propyl ester → HCID 13506661, compound

HRID 1583294Notes

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:33])([O:29][CH2:30][CH2:31][CH3:32])[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:33])[CH2:31][CH3:32]

Participants

Reactant 2

HCID 13506638Carbonic acid, 1-chloroethyl propyl ester

HCID 54676228Piroxicam

Product 1

HCID 13506661HCID 13506661, compound

Procedure

By the procedure of Example 6, piroxicam (3.00 g, 9.1 mmol) and alpha-chloroethyl propyl carbonate (4.52 g, 27.2 mmol) were converted to chromatographed title product, 3.47 g pale yellow foam (7.5 mmol, 83.0%) which gave 3.00 g white crystals from isopropyl alcohol: mp 150°-151° C.; IR (KBr) 1760, 1678 cm-1 : 1H NMR (CDCl3) delta 0.84 (t, J=7 Hz, 3H), 1.46-1.65 (m, 2H), 1.75 (d, J=6 Hz, 3H), 3.11 (s, 3H), 3.97 (t, J=7 Hz, 2H), 6.35 (q, J=6 Hz, 1H), 7.04-7.16 (m, 1H), 7.62-7.97 (m, 5H), 8.30-8.41 (m, 2H), 9.40 (br s, 1H): precise mass calcd for C21H23N3O7S m/e 461.1264, found 461.1260.

Sources & evidence

ORD record: ord-7cd6ad0c714e49b4abfd20bc697ded29
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04551452

Reaction notes

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