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Triphenylphosphine → HCID 22139265, compound

HRID 1825756
Notes
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Reaction equation

HRID 1825756 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].O[C:9]1[CH:19]=[CH:18][C:12]2[NH:13][C:14](=[O:17])[CH2:15][S:16][C:11]=2[CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][O:6][C:9]1[CH:19]=[CH:18][C:12]2[NH:13][C:14](=[O:17])[CH2:15][S:16][C:11]=2[CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 766463-(Dimethylamino)-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 8200317-hydroxy-2H-1,4-benzothiazin-3(4H)-one

Product 1

HCID 22139265HCID 22139265, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

N,N-dimethyl-3-aminopropanol (0.27 g, 5.2 mmol) was added to a mixture of 7-hydroxy-2H-1,4-benzothiazin-3(4H)-one (0.95 g, 5.2 mmol) and triphenylphosphine (1.37 g, 5.2 mmol) in dry tetrahydrofurane (30 ml) under nitrogen atmosphere, followed by diethyl azodicarboxylate (1 g, 5.7 mmol). The mixture was stirred at room temperature for 48 h, concentrated in vacuo, and the product was purified by silica gel chromatography using dichloromethane:methanol gradient of (9:1) to (7:3) as the mobile phase. Yield 1.1 g (75%) mp 120–121° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7c01cc17f5624ac3b25c08fd54dc16e7
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07049312B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes