1,3-Propanediol → HCID 57049612, compound

HRID 442922Notes

Reaction equation

HRID 442922 reaction equation
[N:1]1[S:2][N:3]=[C:4]2[C:9]([S:10]([O:13][C:14]3[CH:15]=[C:16]([OH:21])[CH:17]=[C:18]([CH3:20])[CH:19]=3)(=[O:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=12.C(P(CCCC)CCCC)CCC.[CH2:35](O)[CH2:36][CH2:37][OH:38].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[N:1]1[S:2][N:3]=[C:4]2[C:9]([S:10]([O:13][C:14]3[CH:15]=[C:16]([CH:17]=[C:18]([CH3:20])[CH:19]=3)[O:21][CH2:35][CH2:36][CH2:37][OH:38])(=[O:11])=[O:12])=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

7

Reactant 4

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 54444075HCID 54444075, compound

Product 1

HCID 57049612HCID 57049612, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 3-(benzo-2,1,3-thiadiazole-4-sulfonyloxy)-5-methylphenol (645 mg, 2.0 mmol), as prepared in the preceding step, tri-n-butylphosphine (607 mg, 3.0 mmol) and 1,3-propanediol (760 mg, 10 mmol) in anhydrous tetrahydrofuran (20 mL) was added 1,1'-(azodicarbonyl)dipiperidine (757 mg, 3.0 mmol). The mixture was stirred at ambient temperature overnight. Hexane (30 mL) was added to the mixture, and the precipitates were removed by filtration. The filtrate was evaporated in vacuo, and the residue was purified by flash column chromatography (1:1 hexane/ethyl acetate) to give the title compound as a pale yellow oil (615 mg, 82%). 1H-NMR (300 MHz, CDCl3) δ 8.35 (d, J=8.7 Hz, 1H), 8.26 (d, J=7.1 Hz, 1H), 7.72 (t, J=8.8 Hz, 1H), 6.59 (s, 1H), 6.46 (s, 1H), 6.43 (s, 1H), 3.97 (t, J=6.0 Hz, 2H), 3.80 (t, J=6.0 Hz, 2H), 2.21 (s, 3H), 1,96 (m, 2H), 1.65 (br s, 1H).

Workup

  1. customthe precipitates were removed by filtration
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was purified by flash column chromatography (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5f215273cdba41239e38ecc00bdb7bb2
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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