Nitrogen → HCID 20516515, compound

HRID 1902246Notes

Reaction equation

HRID 1902246 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([CH2:10][CH3:11])[CH:7]=[CH:6][C:5]=1[S:12][CH:13]1[CH2:18][CH2:17][O:16][C:14]1=[O:15])([OH:3])=O.N#N>C(OC(=O)C)(=O)C.C(N(CC)CC)C>[CH2:10]([C:8]1[CH:7]=[CH:6][C:5]2[S:12][C:13]3([C:1](=[O:3])[C:4]=2[CH:9]=1)[CH2:18][CH2:17][O:16][C:14]3=[O:15])[CH3:11]

Participants

5

Reactant 2

HCID 947NitrogenHCID 15575163HCID 15575163, compound

Product 1

HCID 20516515HCID 20516515, compound

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of α-[(2-carboxy-4-ethylphenyl)thio]-γ-butyrolactone (1.0 g) in acetic anhydride (30 ml) and triethylamine (6 ml) was heated at 130° C. for 30 minutes under a stream of N2 gas with stirring. The mixture was evaporated in vacuo. The resulting residue was submitted to column chromatography on silica gel (20 g) and charcoal (5 g) eluting with CHCl3 to give 5-ethyl-4',5'-dihydrospiro[benzo[b]thiophene-2(3H),3'(2'H)-furan]-3,2'-dione as colorless oil. Anal. Calcd. for C13H12O3S: C, 62.88; H, 4.87. Found: C, 62.83; H, 4.83.

Workup

  1. customThe mixture was evaporated in vacuo
  2. washeluting with CHCl3

Sources & evidence

ORD record
ord-73f519756f6b49bfb943c178927d6ea4
Source dataset
uspto-grants-1982_12
Patent number
US04362740

Reaction notes

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