1-Chloroethyl Cyclohexyl Carbonate → HCID 13506662, compound

HRID 1583295Notes

Reaction equation

HRID 1583295 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:36])([O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[O:25][CH:26](Cl)[CH3:27]>>[CH:30]1([O:29][C:24]([O:25][CH:26]([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])[CH3:27])=[O:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 112295291-Chloroethyl Cyclohexyl CarbonateHCID 54676228Piroxicam

Product 1

HCID 13506662HCID 13506662, compound

Procedure

By the procedure of Example 6, piroxicam (3.00 g, 9.1 mmol) and alpha-chloroethyl cyclohexyl carbonate (5.37 g, 26.1 mmol) were converted to chromatographed title product, 3.85 g pale yellow foam (7.7 mmol, 84.7%) which gave 2.45 g white crystals from toluene/hexane: mp 142°-144° C.; IR (KBr) 1749, 1682 cm-1 ; 1H NMR (CDCl3) delta 0.99-1.93 (br m, 10 H), 1.76 (d, J=6 Hz, 3H), 3.11 (s, 3H), 4.40-4.58 (br m, 1H), 6.36 (q, J=6 Hz, 1H), 7.06-7.18 (m, 1H), 7.62-7.97 (m, 5H), 8.32-8.43 (m, 2H), 9.40 (br s, 1H); precise mass calcd for C24H27N3O7S m/e 501.1576, found 501.1613.

Sources & evidence

ORD record
ord-1d4e4c7e722e40c0b07acb2b43a0120c
Source dataset
uspto-grants-1985_11
Patent number
US04551452

Reaction notes

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