Pentachlorophenol → HCID 54166524, compound

HRID 329254Notes

Reaction equation

HRID 329254 reaction equation
[C:1]([CH2:20][CH2:21][C:22]([OH:24])=[S:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:25][C:26]1[C:31](O)=[C:30]([Cl:33])[C:29]([Cl:34])=[C:28]([Cl:35])[C:27]=1[Cl:36].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[Cl:25][C:26]1[C:31]([O:24][C:22](=[S:23])[CH2:21][CH2:20][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:30]([Cl:33])[C:29]([Cl:34])=[C:28]([Cl:35])[C:27]=1[Cl:36]

Participants

5

Reactant 3

HCID 992PentachlorophenolHCID 10868DicyclohexylcarbodiimideHCID 178526179HCID 178526179, compound

Product 1

HCID 54166524HCID 54166524, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-Tritylthiopropionic acid [1.0 g, 2.87 mmoles, described by R. C. Hiskey and M. A. Harpold, J. Org. Chem., 33, 559 (1968)] is dissolved in dry tetrahydrofuran (25 ml) and pentachlorophenol (0.765 g, 2.87 mmoles) is added. The mixture is cooled to 0° C, dicyclohexylcarbodiimide (0.596 g, 2.87 mmoles) is added and the reaction is stirred for 1 hr at 0° C and 1 hr at 25° C. The reaction mixture is then cooled to 0° C, filtered and the filtrate is evaporated under reduced pressure. The residue is crystallized from ethyl acetate to give the title compound, mp 154°-156° C.

Workup

  1. temperatureThe reaction mixture is then cooled to 0° C
  2. filtrationfiltered
  3. customthe filtrate is evaporated under reduced pressure
  4. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-30f6c3c3b9434b6592e2105aec6b0c64
Source dataset
uspto-grants-1977_04
Patent number
US04020157

Reaction notes

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