Methanesulfonyl chloride → HCID 13799775, compound

HRID 1906379Notes

Reaction equation

HRID 1906379 reaction equation
Cl.[NH2:2][C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:4]#[N:5].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:7]1([C:3]([NH:2][S:14]([CH3:13])(=[O:16])=[O:15])([CH3:6])[C:4]#[N:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 20211717HCID 20211717, compound2×

Product 1

HCID 13799775HCID 13799775, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2 g (0.0109 mole) 2-amino-2-phenyl-propionitrile hydrochloride (the product of Example 11) in methylene chloride (about 50 ml), 2.6 g (0.0218 mole) 4-dimethylaminopyridine was added, followed by 1.3 g (0.0109 mole) methanesulfonyl chloride in 10 ml methylene chloride in an exothermic addition. The reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into 100 ml ice water. The layers were separated using a separatory funnel. The organic (methylene chloride) phase was washed twice with water, dried over magnesium sulfate, filtered and stripped to give 2 g of the above-identified product as an orange slush.

Workup

  1. customThe layers were separated
  2. washThe organic (methylene chloride) phase was washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-3b282d2417934b17874ca3b515f6671c
Source dataset
uspto-grants-1987_03
Patent number
US04652556

Reaction notes

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