Potassium Bromide → 4-[1-(Hexyloxycarbonyloxy)ethoxy]-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide

HRID 1583298Notes

Reaction equation

HRID 1583298 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][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[O:25][CH:26](Cl)[CH3:27].C(O)(C)C.CCCCCC.[K+].[Br-]>>[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:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 4

HCID 253877Potassium BromideHCID 135066371-Chloroethyl Hexyl CarbonateHCID 21585144Isopropanol hexaneHCID 54676228Piroxicam

Product 1

HCID 135066674-[1-(Hexyloxycarbonyloxy)ethoxy]-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide

Procedure

By the procedure of Example 11, piroxicam (3.00 g, 9.1 mmol) and alpha-chloroethyl hexyl carbonate (2.85 g, 13.6 mmol) were converted to chromatographed title product, isolated as a yellow solid which was crystallized from isopropyl alcohol/hexane (280 mg, 0.5 mmol, 6.1%): mp 86°-87° C.; IR (KBr) 1764, 1678 cm-1 ; 1H NMR (CCl3) delta 0.87 (t, J=7 Hz, 3H), 1.05-1.39 (m, 6H), 1.41-1.60 (m, 2H), 1.75 (d, J=6 Hz, 3H), 3.10 (s, 3H), 4.00 (t, J=7 Hz, 2H), 6.36 (q, J=6 Hz, 1H), 7.06-7.17 (m, 1H), 7.63-7.86 (m, 5H), 8.31-8.42 (m, 2H), 9.39 (br s, 1H); precise mass calcd for C24H29N3O7S m/e 503.1737, found 503.1761.

Workup

  1. customto chromatographed title product
  2. customisolated as a yellow solid which

Sources & evidence

ORD record
ord-94f620f29ff141b5b1b61451c538b220
Source dataset
uspto-grants-1985_11
Patent number
US04551452

Reaction notes

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