Triphenylphosphine → HCID 14098951, compound

HRID 2232063Notes

Reaction equation

HRID 2232063 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]1[C:15](=[O:16])[N:14]([CH3:17])[C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=2[S:11]1.[Br:22][CH2:23][CH2:24][CH2:25]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Br:22][CH2:23][CH2:24][CH2:25][O:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]1[C:15](=[O:16])[N:14]([CH3:17])[C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=2[S:11]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11066567HCID 11066567, compound

Product 1

HCID 14098951HCID 14098951, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (-)-3,4-dihydro-2-(2-hydroxy-5-methoxyphenyl)-4-methyl-3-oxo-2H-1,4-benzothiazine (6.3 g), which was prepared by the process (ii), in anhydrous tetrahydrofuran (70 ml), 3-bromo-1-propanol (8.8 g), triphenylphosphine (16.6 g) and then diethyl azodicarboxylate (10.0 ml) were added. The mixture was stirred for 2 hours under nitrogen atmosphere and concentrated in vacuo. The residue was purified by the silica gel column chromatography to give 4.5 g (51%) of (-)-3,4-dihydro-2-[2-(3-bromopropoxy)-5-methoxyphenyl]-4-methyl-3-oxo-2H-1,4-benzothiazine.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-db349940c74d49948f5053dca475841a
Source dataset
uspto-grants-1988_11
Patent number
US04786635

Reaction notes

Loading…