Water → Ethyl 5-chloro-2-[(chloroacetyl)amino]-6-[(2,2-dimethylpropanoyl)amino]nicotinate

HRID 1168263Notes

Reaction equation

HRID 1168263 reaction equation
[NH2:1][C:2]1[N:12]=[C:11]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:10]([Cl:20])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].[Cl:27][CH2:28][C:29](Cl)=[O:30].O>O1CCCC1>[Cl:20][C:10]1[C:11]([NH:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:18])[CH3:17])=[N:12][C:2]([NH:1][C:29](=[O:30])[CH2:28][Cl:27])=[C:3]([CH:9]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 12088089Ethyl 2-amino-5-chloro-6-[(2,2-dimethylpropanoyl)amino]nicotinate

Product 1

HCID 22992210Ethyl 5-chloro-2-[(chloroacetyl)amino]-6-[(2,2-dimethylpropanoyl)amino]nicotinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-amino-5-chloro-6-[(2,2-dimethylpropanoyl)amino]nicotinate (EXAMPLE 1, METHOD A, Step 2, 5 g, 16.7 mmol) in tetrahydrofuran (150 mL) were added potassium carbonate (5.1 g, 36.6 mmol) and chloroacetyl chloride (2.7 mL, 33.3 mmol) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 2 h and at room temperature for 15 h. After addition of water, the mixture was extracted with ethyl acetate and washed with brine. The combined organic layer was dried over sodium sulfite and concentrated to give the title compound as a pale yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe combined organic layer was dried over sodium sulfite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6857a770d6c4438e9b2157cbf77ea30d
Source dataset
uspto-grants-2003_09
Patent number
US06624162B2

Reaction notes

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