Hydrochloric Acid → HCID 21920085, compound

HRID 1592988Notes

Reaction equation

HRID 1592988 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-dd068595de564abd8dc08e06b756626e
Source dataset
uspto-grants-2007_11
Patent number
US07294639B2

Reaction notes

Loading…