Chloromethyl benzoate → HCID 13506659, compound

HRID 1583306Notes

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

Participants

Reactant 3

HCID 79257Chloromethyl benzoate

HCID 253877Potassium Bromide

HCID 54676228Piroxicam

Product 1

HCID 13506659HCID 13506659, compound

Procedure

By the procedure of Example 6, piroxicam (3.33 g, 10.1 mmol) and chloromethyl benzoate (4.29 g, 25.0 mmol) were converted to chromatographed title product, 2.3 g (4.9 mmol), 48.9%) white foam which gave white crystals from isopropyl alcohol: mp 149°-150° C.; IR (KBr) 1745, 1687 cm-1 ; 1H NMR (CDCl3) delta 3.07 (s, 3H), 5.89 (s, 2H), 6.97-7.08 (m, 1H), 7.19-7.35 (m, 2H), 7.35-7.63 (m, 2H), 7.63-7.99 (m, 6H), 8.22-8.35 (m, 2H), 9.22 (br s, 1H); precise mass calcd for C23H19N3O6S m/e 465.1001, found 465.1051

Workup

customto chromatographed title product, 2.3 g (4.9 mmol), 48.9%) white foam which
customgave white crystals from isopropyl alcohol

Sources & evidence

ORD record: ord-f0b81f69c86c415bbe06df44a5415048
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04551452

Reaction notes

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