Hydrochloric Acid → HCID 21920085, compound

HRID 1244660Notes

Reaction equation

HRID 1244660 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[CH2:23]([O:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]=[C:37]=[O:38])=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].Cl>ClCCl>[O:21]=[C:19]1[NH:18][C:17](=[O:22])[CH:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:1])[C:37]([NH:36][C:33]4[CH:32]=[CH:31][C:30]([O:29][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:35][CH:34]=4)=[O:38])[CH:4]=3)=[CH:14][CH:13]=2)[S:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27694231-(Hexyloxy)-4-isocyanatobenzeneHCID 21920157HCID 21920157, compound

Product 1

HCID 21920085HCID 21920085, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.67 g (2.14 mmol) of 5-(3′-methylaminobiphenyl-4-ylmethyl)thiazolidine-2,4-dione in 20 ml of dichloromethane is introduced into a 50 ml round-bottomed flask. 1 g (4.3 mmol) of 1-hexyloxy-4-isocyanatobenzene is added and the mixture is heated under reflux for 16 hours. The reaction medium is poured at room temperature over a 1 N HCl solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulphate. After evaporation of the solvents, the product obtained is purified by chromatography on silica gel (eluent: heptane/ethyl acetate=3/2). 0.78 g (68%) of 1-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-3-(4-hexyloxyphenyl)-1-methylurea is obtained in the form of a white powder having a melting point of 146–148° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 16 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. customAfter evaporation of the solvents
  7. customthe product obtained
  8. customis purified by chromatography on silica gel (eluent: heptane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-1a8a7738eec945198317776372c17169
Source dataset
uspto-grants-2006_10
Patent number
US07122564B2

Reaction notes

Loading…