3-Chloropropionitrile → HCID 178427654, compound

HRID 974426Notes

Reaction equation

HRID 974426 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].O.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1.[Cl:18][CH2:19][CH2:20][C:21]#[N:22]>C(Cl)Cl.CC(C)=O>[C:7]1([CH3:17])[CH:8]=[CH:9][C:10]([S:13]([OH:16])(=[O:14])=[O:15])=[CH:11][CH:12]=1.[S:1]([NH:5][C:21](=[NH:22])[CH2:20][CH2:19][Cl:18])(=[O:3])(=[O:2])[NH2:4]

Participants

6

Reactant 3

HCID 109633-ChloropropionitrileHCID 82267SulfamideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 178427654HCID 178427654, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
57.5 °C

Procedure

Sulfamide (9.6 g, 0.1 mole) was added to a suspension of p-toluenesulfonic acid monohydrate (38.0 g, 0.2 mole) in 3-chloropropionitrile (51.3 g, 0.6 mole). The suspension was heated at 55-60° C., for 18 hours. At the end of the heating period, the mixture was cooled to room temperature, diluted with methylene chloride (150 ml), and filtered. The solid, thus obtained, was suspended in acetone (50 ml) and the suspension filtered and the product dried.

Workup

  1. temperatureAt the end of the heating period, the mixture was cooled to room temperature
  2. filtrationfiltered
  3. customThe solid, thus obtained
  4. filtrationthe suspension filtered
  5. customthe product dried

Sources & evidence

ORD record
ord-260e9ecfdaad4981b882b1e396e4e29f
Source dataset
uspto-grants-1991_11
Patent number
US05068405

Reaction notes

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