Water → HCID 131719754, compound

HRID 1081961Notes

Reaction equation

HRID 1081961 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH:13][CH2:14][C@H:15]1[S:19][C@H:18]([OH:20])[CH2:17][S:16]1.[OH2:21]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:13][CH2:14][C@H:15]2[S:19][C@H:18]([O:20][C:8](=[O:9])[C:7]3[CH:11]=[CH:12][C:4]([N+:1]([O-:2])=[O:21])=[CH:5][CH:6]=3)[CH2:17][S:16]2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 85024-Nitrobenzoyl chlorideHCID 88408483HCID 88408483, compound

Product 1

HCID 131719754HCID 131719754, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

p-Nitrobenzoyl chloride (4.72 g, 25.42 mmol) was added to a solution of cis and trans-2-hydroxymethyl-4-hydroxy-1,3-dithiolane (1.38 g, 9.08 mmol) in dry pyridine (50 mL) at 0° C. the reaction mixture was then placed in the refrigerator for 18 h. The reaction mixture was then poured into water and extracted with methylene chloride (3X). The combined organic extracts were washed with water, brine, dried and concentrated to give a yellow solid, 3.68 g (90%). 1H NMR (CDCl3) (300 MHz) δ: (8.27 (m, 8H, Ar-H), 6.86+6.81 (dd's, 1H, 3Hz, 2Hz, C4-H), 4.96+4.87 (t's, 1H, 7Hz, C2--H), 4.47 (m, 2H, CH2OAr), 3.5 (m, 2H, C5--H).

Workup

  1. extractionextracted with methylene chloride (3X)
  2. washThe combined organic extracts were washed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. customto give a yellow solid, 3.68 g (90%)

Sources & evidence

ORD record
ord-f3e8c59589b34d2f8357cbc7233e6d5e
Source dataset
uspto-grants-1996_12
Patent number
US05587480

Reaction notes

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