Chlorosuccinimide → [2-[(3-Carbamoyl-5-chloro-2-thienyl)amino]-1,1-dimethyl-2-oxo-ethyl]acetate

HRID 1049866Notes

Reaction equation

HRID 1049866 reaction equation
[C:1]([C:4]1[CH:8]=[CH:7][S:6][C:5]=1[NH:9][C:10](=[O:18])[C:11]([O:14][C:15](=[O:17])[CH3:16])([CH3:13])[CH3:12])(=[O:3])[NH2:2].C1C(=O)N([Cl:26])C(=O)C1>CC(O)=O.O>[C:1]([C:4]1[CH:8]=[C:7]([Cl:26])[S:6][C:5]=1[NH:9][C:10](=[O:18])[C:11]([O:14][C:15](=[O:17])[CH3:16])([CH3:12])[CH3:13])(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 117717784[2-[(3-Carbamoyl-2-thienyl)amino]-1,1-dimethyl-2-oxo-ethyl]acetate

Product 1

HCID 117717725[2-[(3-Carbamoyl-5-chloro-2-thienyl)amino]-1,1-dimethyl-2-oxo-ethyl]acetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Intermediate 10 (78.5 g, 291 mmol) is dissolved in AcOH (850 mL). To the resulting suspension, NCS (42.9 g, 320 mmol) is added. The mixture is stirred at room temperature, after which it is evaporated to give a slurry. This slurry is taken up in water to give a suspension that is filtered. Resulting precipitate is dried in the vacuum oven and used as such.

Workup

  1. customafter which it is evaporated
  2. customto give a slurry
  3. customto give a suspension that
  4. filtrationis filtered
  5. customResulting precipitate
  6. customis dried in the vacuum oven

Sources & evidence

ORD record
ord-ca5eb0717c5b459fa86f192bc66be5fe
Source dataset
uspto-grants-2016_07
Patent number
US09382254B2

Reaction notes

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