Triphenylphosphine → HCID 14650629, compound

HRID 982256Notes

Reaction equation

HRID 982256 reaction equation
S1C=C(O)C=NC1.N(C(OCC)=O)=NC([O-])=O.[OH:18][CH:19]([CH2:36]O)[CH:20]([NH:27][C:28](=[S:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:29]1([C:28]2[S:35][CH2:36][CH:19]([OH:18])[CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:27]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 20069303HCID 20069303, compoundHCID 86599450N-ethoxycarbonyliminocarbamateHCID 86744628HCID 86744628, compound

Product 1

HCID 14650629HCID 14650629, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

(4RS, 5RS)-2,4-diphenyl-5,6-dihydro-4H, 1,3-thiazin-5-ol may be prepared in the following manner: a solution of ethyl azodicarboxylate (1.1 g) dissolved in anhydrous tetrahydrofuran (5 cc) is added dropwise at a temperature in the region of 0° C. to a solution, maintained under an argon atmosphere, of N-[(1RS, 2RS)-2,3-dihydroxy-1-phenylpropyl]thiobenzamide (1.7 g) and triphenylphosphine (1.57 g) in anhydrous tetrahydrofuran (17 cc). The solution obtained is stirred at a temperature in the region of 20° C. for 16 hours and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is purified by chromatography on silica (0.063-0.2 mm; 100 g) contained in a column 2.5 cm in diameter [(eluent: cyclohexane/ethyl acetate (3:7 by volume)], collecting 20-cc fractions. Fractions 5 to 11 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in diisopropyl ether, (4RS, 5RS)-2,4-diphenyl-5,6-dihydro-4H-1,3-thiazin-5-ol (0.86 g), m.p. 142° C. is obtained.

Workup

  1. additionis added dropwise at a temperature in the region of 0° C. to a solution
  2. customThe solution obtained
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is purified by chromatography on silica (0.063-0.2 mm; 100 g)
  5. customcyclohexane/ethyl acetate (3:7 by volume)], collecting 20-cc fractions
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  7. customAfter recrystallization in diisopropyl ether

Sources & evidence

ORD record
ord-7b76a55e025646b394a6537129e0a82a
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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