Chlorosuccinimide → HCID 178445673, compound

HRID 1458659Notes

Reaction equation

HRID 1458659 reaction equation
[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[CH:17]=[C:16]([I:18])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl:19]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[C:1]([C@@H:5]1[CH2:6][CH2:7][C@H:8]([NH:11][C:12]2[C:17]([Cl:19])=[C:16]([I:18])[N:15]=[CH:14][N:13]=2)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178445670HCID 178445670, compound

Product 1

HCID 178445673HCID 178445673, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.6 g (10 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-6-iodopyrimidine and 2.0 g of N-chlorosuccinimide were heated at reflux for 8 hours in 15 ml of chloroform. After cooling to room temperature, the mixture was extracted by stirring with dilute sodium hydroxide solution and water and the organic phase was dried and concentrated. The residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate 4:1) to give first of all 2.3 g (58.4% of theory) of product (a colorless oil which gradually crystallized, m.p. 89° to 90° C.) and, finally, 1.0 g of unreacted starting material.

Workup

  1. extractionthe mixture was extracted
  2. customthe organic phase was dried
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate 4:1)
  5. customto give first of all 2.3 g (58.4% of theory) of product (a colorless oil which
  6. customgradually crystallized

Sources & evidence

ORD record
ord-f60c18af3c0b4ca9ac9b4f706abce17d
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

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