Potassium Bromide → HCID 13506651, compound

HRID 1583301Notes

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:31][CH:32](Cl)[CH3:33])(=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C1(C)C=CC=CC=1.CCCCCC.[K+].[Br-]>>[C:24]([O:31][CH:32]([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])[CH3:33])(=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

Reactant 4

HCID 253877Potassium Bromide

HCID 3230761-chloroethyl hexanoate

HCID 21889329Toluene hexane

HCID 54676228Piroxicam

Product 1

HCID 13506651HCID 13506651, compound

Procedure

By the procedure of Example 11, piroxicam (2.00 g, 6.0 mmol) and alpha-chloroethyl hexanoate (3.51 g, 19.6 mmol) were converted to chromatographed title product as yellow oil which was crystallized from toluene/hexane (1.21 g, 2.5 mmol, 42.1%): mp 62°-65° C.; IR (KBr) 1755, 1676 cm-1 ; 1H NMR (CDCl3) delta 0.81 (t, J=7 Hz, 3H), 1.00-1.30 (m 4H), 1.35-1.53 (m, 2H), 1.73 (d, J=6 Hz, 3H), 2.08-2.32 (m, 2H), 3.12 (s, 3H), 6.39 (q, J=6 Hz, 1H), 7.05-7.32 (m, 1H), 7.57-7.95 (m, 5H), 8.30-8.43 (m, 2H), 9.58 (br s, 1H): precise mass calcd for C23H28N3O6S m/e (P+ +H) 474.1703, found 474.1645.

Workup

customto chromatographed title product as yellow oil which

Sources & evidence

ORD record: ord-43f7070306514fa59773127213bae6df
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04551452

Reaction notes

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