HCID 23301804, compound → HCID 23301864, compound

HRID 1953015Notes

Reaction equation

HRID 1953015 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)=[O:6].[K].CC(C)([O-])C>CN(C)C=O>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])=[CH:10][CH:11]=1)#[N:16]

Participants

4

Reactant 2

HCID 23301804HCID 23301804, compoundHCID 50987170Potassium tertbutoxide

Product 1

HCID 23301864HCID 23301864, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 20.0 g (84.1 mMol) of 1-(2-chloroethyl)-3-[(4-cyanophenyl)methyl]-urea in 200 ml of anhydrous dimethylformamide were added, in batches and at ambient temperature, 11.2 g (99.8 mMol) of potassium-tert.butoxide and the mixture was then stirred for 2 hours at +40° C. The reaction mixture was evaporated down in vacuo, the residue remaining was distributed between water and ethyl acetate, the organic phase was dried over sodium sulphate, clarified over activated charcoal and evaporated down in vacuo once more. The residue was triturated with tert.butyl-methylether, suction filtered and dried in a vacuum dryer. 3.0 g (18% of theory) of colourless crystals were obtained, Mp. 117-118° C.

Workup

  1. customThe reaction mixture was evaporated down in vacuo
  2. dry with materialthe organic phase was dried over sodium sulphate
  3. customevaporated down in vacuo once more
  4. customThe residue was triturated with tert.butyl-methylether, suction
  5. filtrationfiltered
  6. customdried in a vacuum dryer
  7. custom3.0 g (18% of theory) of colourless crystals were obtained

Sources & evidence

ORD record
ord-4e5d6a9bbd3f469d86e5a26add6c37a3
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

Loading…