Toluene → HCID 86584758, compound

HRID 1634065Notes

Reaction equation

HRID 1634065 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[CH:14][C:11]=2[CH:12]=O)=[CH:4][CH:3]=1.[S:27]1[CH2:33][C:31](=[O:32])[N:30]([CH2:34][C:35]([OH:37])=[O:36])[C:28]1=[S:29].C(O)(=O)C.N1CCCCC1.C1(C)C=CC=CC=1>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[CH:14][C:11]=2[CH:12]=[C:33]2[S:27][C:28](=[S:29])[N:30]([CH2:34][C:35]([OH:37])=[O:36])[C:31]2=[O:32])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 797933-Thiazolidineacetic acid, 4-oxo-2-thioxo-HCID 9793820Piperidine, acetateHCID 18677290HCID 18677290, compound

Product 1

HCID 86584758HCID 86584758, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

125 mg (0.323 mmol) of 2,5-bis-(4-chlorophenyl-methoxy)benzaldehyde, 68.3 mg (0.355 mmol) of rhodanine-3-acetic acid, 18 mg (0.125 mmol) of piperidine acetate and 10 ml of toluene were heated on a water separator under a nitrogen atmosphere for 4 hours. Subsequently, the reaction mixture was evaporated, the residue was taken up in ethyl acetate, washed several times with water, dried and again evaporated. The residue was triturated with diethyl ether and filtered off under suction: 125 mg (69%) of the title compound; 1HNMR (DMSO-d6, 250 MHz) δ 7.92 (s, 1H), 7.49 (m, 8H), 7.20 (m, 2H), 7.00 (m, 1H), 5.22 (s, 2H), 5.18 (s, 2H), 4.57 (s, 2H); TLC (toluene/methyl ethyl ketone/glacial acetic acid (72:20:8)): Rf=0.51.

Workup

  1. customSubsequently, the reaction mixture was evaporated
  2. washwashed several times with water
  3. customdried
  4. customagain evaporated
  5. customThe residue was triturated with diethyl ether
  6. filtrationfiltered off under suction

Sources & evidence

ORD record
ord-85a6e4dbaf49429bac0c223777548ba7
Source dataset
uspto-grants-2003_01
Patent number
US06506755B2

Reaction notes

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