Phthalimide → N-(10-Methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)phthalimide

HRID 1059423Notes

Reaction equation

HRID 1059423 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14]O)[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:16]=[CH:17][CH:18]=[N:19][C:5]1=2.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][N:24]3[C:23](=[O:25])[C:22]4=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]4[C:20]3=[O:30])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:16]=[CH:17][CH:18]=[N:19][C:5]1=2

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1126581710-Methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine-8-methanol

Product 1

HCID 18670612N-(10-Methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)phthalimideYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.32 g of (10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)methanol, 2.12 g of phthalimide and 3.77 g of triphenylphosphine in tetrahydrofuran (50 ml) was ice-cooled and 2.24 ml of diethyl azodicarboxylate was dropped thereinto. After stirring at room temperature for 1 hour, the solvent was distilled off under reduced pressure and diethyl ether was added to the residue. Then it was subjected to ultrasonication and the crystals thus precipitated were taken up by filtration to thereby give 2.6 g of the title compound as pale yellow crystals.

Workup

  1. temperaturecooled
  2. distillationthe solvent was distilled off under reduced pressure and diethyl ether
  3. additionwas added to the residue
  4. customThen it was subjected to ultrasonication
  5. customthe crystals thus precipitated
  6. filtrationwere taken up by filtration

Sources & evidence

ORD record
ord-9bb989bb16214cebb991b4fffb7dc45c
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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