Thionyl Chloride → HCID 22024658, compound

HRID 501008Notes

Reaction equation

HRID 501008 reaction equation
[Br:1][C:2]1[C:3]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10]O)=[N:4][CH:5]=[N:6][CH:7]=1.S(Cl)(Cl)=O>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[C:3]2[N:4]([CH2:10][CH:9]([CH2:12][CH3:13])[N:8]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22024679HCID 22024679, compound

Product 1

HCID 22024658HCID 22024658, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

2-[(5-Bromo-4-pyrimidinyl)amino]-1-butanol (3.3 g) was dissolved in xylene (27 mL), then thionyl chloride (4.9 mL) was added thereto, and the mixture was heated under stirring at 100° C. for 1 day. The precipitated crystals were collected by filtration and suspended in a 1M aqueous sodium carbonate solution. This mixture was extracted with dichloromethane to give the crude title compound (3.0 g) as an orange oil. This title compound was used in the next reaction without purification.

Workup

  1. temperaturethe mixture was heated
  2. filtrationThe precipitated crystals were collected by filtration
  3. extractionThis mixture was extracted with dichloromethane

Sources & evidence

ORD record
ord-281fe9257f52469ab646f0b24a9f47fc
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

Loading…