Water → HCID 66748417, compound

HRID 1405870Notes

Reaction equation

HRID 1405870 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([NH2:17])=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:19][CH2:20][S:21](Cl)(=[O:23])=[O:22].O>CN(C)C(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3=[N:17][S:21](=[O:23])(=[O:22])[CH2:20][CH2:19][N:13]3[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 64088556HCID 64088556, compound

Product 1

HCID 66748417HCID 66748417, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 3-(4-tert-butylphenyl)pyridin-2-amine (301 mg) in N,N-dimethylacetoamide (4 mL) was added dropwise to 2-chloroethanesulfonyl chloride (437 mg) and additional N,N-dimethylacetoamide (1 mL) was used to complete the addition of above solution. After being stirred at 60° C. for 3 hr, the mixture was cooled to room temperature. Water (10 mL) was added dropwise to the reaction mixture and the whole was stirred at room temperature for 0.5 hr. The precipitate was collected by filtration, washed with water (10 mL) and diisopropyl ether (3 mL), and dried in vacuo at 60° C. to give the title compound (366 mg) as an off-white powder.

Workup

  1. additionthe addition of above solution
  2. temperaturethe mixture was cooled to room temperature
  3. stirringthe whole was stirred at room temperature for 0.5 hr
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water (10 mL) and diisopropyl ether (3 mL)
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-f06ec4df23dc41e6b82fa36cdd0a27aa
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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