Toluene → 5-[(2,5-Bis-benzyloxyphenyl)methylene]-4-oxo-2-thioxo-thiazolidine

HRID 1634066Notes

Reaction equation

HRID 1634066 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:25]1[CH2:31][C:29](=[O:30])[NH:28][C:26]1=[S:27].C(O)(=O)C.N1CCCCC1.C1(C)C=CC=CC=1>O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][C:10]=1[CH:11]=[C:31]1[S:25][C:26](=[S:27])[NH:28][C:29]1=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 1201546RhodanineHCID 35303992,5-Bis(benzyloxy)benzaldehydeHCID 9793820Piperidine, acetate

Product 1

HCID 734559975-[(2,5-Bis-benzyloxyphenyl)methylene]-4-oxo-2-thioxo-thiazolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.59 g (5 mmol) of 2,5-bis-benzyloxybenzaldehyde, 0.73 g (5.5 mmol) of rhodanine, 0.29 g (2 mmol) of piperidine acetate and 40 ml of toluene were heated on a water separator under a nitrogen atmosphere for 1.5 hours. After cooling, the yellow crystals were filtered off under suction, washed with toluene and diethyl ether and dried in a vacuum: 1.34 g (62%) of 5-[(2,5-bis-benzyloxyphenyl)methylene]-4-oxo-2-thioxo-thiazolidine; 1HNMR (DMSO-d6, 250 MHz) δ 13.80 (s, 1H), 7.80 (s, 1H), 6.85-7.50 (m, 13H), 5.19 (s, 2H), 5.10 (s, 2H); TLC (toluene/methyl ethyl ketone/glacial acetic acid (72:20:8)): Rf=0.80.

Workup

  1. temperatureAfter cooling
  2. filtrationthe yellow crystals were filtered off under suction
  3. washwashed with toluene and diethyl ether
  4. customdried in a vacuum

Sources & evidence

ORD record
ord-71230f2f98ef4511a897c5213c856e18
Source dataset
uspto-grants-2003_01
Patent number
US06506755B2

Reaction notes

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