Water → Benzamide, 3-[(chloroacetyl)amino]-

HRID 1586618Notes

Reaction equation

HRID 1586618 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([NH2:12])=[O:11].C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1>[Cl:1][CH2:2][C:3]([NH:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([NH2:12])=[O:11])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 16453-AminobenzamideHCID 6577Chloroacetyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 354108Benzamide, 3-[(chloroacetyl)amino]-Yield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

Chloroacetyl chloride (4 g, 35.4 mmol) was added to a stirred mixture of 3-aminobenzamide (4.0 g 25.9 mmol), K2CO3 (22 g, 159 mmol), water (40 ml), and dioxane (40 ml) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and 25° C. for 16 hours, resulting in a solid precipitate. The precipitate was collected, washed, and dried to yield 4.1 g (75%) of the desired 3-chloroacetamidobenzamide, mp: 210 (D).

Workup

  1. customresulting in a solid precipitate
  2. customThe precipitate was collected
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-a98e22b4419c44c0af6cf3c3b891df30
Source dataset
uspto-grants-1993_06
Patent number
US05215738

Reaction notes

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