Water → HCID 18543578, compound

HRID 990858Notes

Reaction equation

HRID 990858 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[Cl:15])=[O:4].C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][SH:27].O>CN(C)C=O>[Cl:15][C:7]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:6]=1[NH:5][C:3](=[O:4])[CH2:2][S:27][CH2:26][CH2:25][N:24]([CH3:28])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 25798Captamine HydrochlorideHCID 37336412-chloro-N-(2-chloro-4-nitrophenyl)acetamide

Product 1

HCID 18543578HCID 18543578, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of N-(chloroacetyl)-2-chloro-4-nitroaniline (3.01 g) in N,N-dimethylformamide (100 mL) is added powdered sodium carbonate (6.0 g) and 2-dimethylaminoethanethiol hydrochloride (6.0 g). The mixture is stirred for 1 hour at 25° C., poured into water and extracted into ethyl acetate. The ethyl acetate solution is dried over anhydrous potassium carbonate and concentrated under reduced pressure to give an oil. The oil is crystallized from toluene-hexanes (3:1) to yield a pale yellow crystalline solid.

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialThe ethyl acetate solution is dried over anhydrous potassium carbonate
  3. concentrationconcentrated under reduced pressure
  4. customto give an oil
  5. customThe oil is crystallized from toluene-hexanes (3:1)
  6. customto yield a pale yellow crystalline solid

Sources & evidence

ORD record
ord-dc07c2fcf3194ee38cc1a4719ea21262
Source dataset
uspto-grants-2002_10
Patent number
US06462055B2

Reaction notes

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