2-Chloroethyl isocyanate → N-(6-Bromo-2-pyridinyl)-N'-(2-chloroethyl)urea

HRID 32800

Reaction equation

HRID 32800 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[Cl:9][CH2:10][CH2:11][N:12]=[C:13]=[O:14]>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:13]([NH:12][CH2:11][CH2:10][Cl:9])=[O:14])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 58791151N-(6-Bromo-2-pyridinyl)-N'-(2-chloroethyl)ureaYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-2-pyridinamine (1 g, 5.78 mmol) in anh. THF (25 mL), at r.t., under N2, was added 1-chloro-2-isocyanatoethane (1.2 mL, 2.5 eq) and the reaction mixture was stirred at r.t. for 18 hr. The crude mixture was partitioned between CH2Cl2 and water. The phases were separated and the organic layer was dried over anh. Na2SO4. The solids were filtered and the solvent evaporated to give the title compound (1.06 g, 66%) which was used in the next step without further purification.

Workup

  1. customThe crude mixture was partitioned between CH2Cl2 and water
  2. customThe phases were separated
  3. dry with materialthe organic layer was dried over anh. Na2SO4
  4. filtrationThe solids were filtered
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-a57cf86785af40228e02713709f17dc7
Source dataset
uspto-grants-2008_09
Patent number
US07427630B2

Linked notes

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