Dicyclohexylcarbodiimide → HCID 12493406, compound

HRID 2397787Notes

Reaction equation

HRID 2397787 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.Cl.[NH2:17][CH2:18][C:19](O)=[O:20].[NH2:22][C:23]1[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][C:24]=1[C:25](=[N:33][CH2:34][CH2:35][OH:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32]>CN(C)C=O.O.O1CCCC1>[NH2:17][CH2:18][C:19]([NH:22][C:23]1[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][C:24]=1[C:25](=[N:33][CH2:34][CH2:35][OH:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])=[O:20]

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 22316Glycine HydrochlorideHCID 13341587HCID 13341587, compound

Product 1

HCID 12493406HCID 12493406, compoundYield 57.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.5g of N,N'-dicyclohexylcarbodiimide in 100ml of dimethylformamide is added a solution of 2.2g of glycine hydrochloride in 2.2ml of water in a period of about 30 seconds under stirring and ice-cooling. Immediately a solution of 3.4g of 2-{[2-amino-5-bromo-α-(2-fluorophenyl)benzylidene]amino}ethanol in 10ml of tetrahydrofuran is added dropwise to the reaction mixture, and the mixture is stirred for further 3 hours at room temperature. After completion of the reaction, one liter of water is added to the reaction mixture which is extracted once with 100ml and four times with 50ml of benzene. The organic layer is washed with water, dried over anhydrous sodium sulfate, and the solvent is distilled off to give an oily substance, which is purified by chromatography of alumina column and then recrystallized from benzene-n-hexane (3:2 in volume) mixture yielding 2.3g of the desired product melting at 167°-168° C.

Workup

  1. temperatureice-cooling
  2. stirringthe mixture is stirred for further 3 hours at room temperature
  3. additionis added to the reaction mixture which
  4. extractionis extracted once with 100ml and four times with 50ml of benzene
  5. washThe organic layer is washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent is distilled off
  8. customto give an oily substance, which
  9. customis purified by chromatography of alumina column
  10. customrecrystallized from benzene-n-hexane (3:2 in volume) mixture

Sources & evidence

ORD record
ord-f5b10d1ee51847449050d8eabcddf3b1
Source dataset
uspto-grants-1977_05
Patent number
US04022832

Reaction notes

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