Isopropanol → NSC 629243

HRID 1938866Notes

Reaction equation

HRID 1938866 reaction equation
[CH:1]1(N=C=NC2CCCCC2)[CH2:6]CCC[CH2:2]1.[Cl:16][C:17]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[S:28])=[CH:22][C:18]=1[C:19]([OH:21])=[O:20].C(O)(C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:16][C:17]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[S:28])=[CH:22][C:18]=1[C:19]([O:21][CH:1]([CH3:6])[CH3:2])=[O:20]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 10868Dicyclohexylcarbodiimide2×HCID 3001524Benzoic acid, 2-chloro-5-(((1-methylethoxy)thioxomethyl)amino)-

Product 1

HCID 3000477NSC 629243

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

This is the preparation of compound 32 using 1,3-dicyclohexylcarbodiimide. A mixture of 2-chloro-5-[[(1-methylethoxy)thioxomethyl]amino]benzoic acid (2 g, 0.007 mol), isopropyl alcohol (1.3 g, 0.02 mol), 4-dimethylaminopyridine (0.85 g, 0.007 mol) in 25 ml methylene chloride was stirred in an ice bath and 1,3-dicyclohexylcarbodiimide (1.7 g 0.008 mol) added. The mixture was allowed to come to ambient temperature and stirred overnight. The precipitated solid was filtered off and the filtrate washed with dilute hydrochloric acid and aqueous 5% sodium bicarbonate. After drying over magnesium sulfate, filtering and removing the methylene chloride, the product was crystallized from toluene/petroleum ether. Yield 1.2 g m.p. 89° C. A mixed m.p. with authentic compound 32 also gave m.p. 89°-90° C. The N.M.R. spectrum was identical with that of authentic compound 32.

Workup

  1. customto come to ambient temperature
  2. stirringstirred overnight
  3. filtrationThe precipitated solid was filtered off
  4. washthe filtrate washed with dilute hydrochloric acid and aqueous 5% sodium bicarbonate
  5. dry with materialAfter drying over magnesium sulfate
  6. filtrationfiltering
  7. customremoving the methylene chloride
  8. customthe product was crystallized from toluene/petroleum ether

Sources & evidence

ORD record
ord-64662af837f04ca29b2f5a195a054d2b
Source dataset
uspto-grants-1997_12
Patent number
US05693827

Reaction notes

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