Water → HCID 19045060, compound

HRID 1781235Notes

Reaction equation

HRID 1781235 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[Br:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:9]=1[NH2:18].O.[Cl-].[Na+]>CN(C)C1C=CN=CC=1.O1CCCC1.ClCCCC>[Br:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:9]=1[NH:18][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1]

Participants

8

Reactant 4

HCID 962Water2×HCID 5234Sodium ChlorideHCID 12661DiketeneHCID 27753062-Bromo-4-methyl-6-nitroaniline

Product 1

HCID 19045060HCID 19045060, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8005Butyl ChlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of diketene (57.71 mL, 748.2 mmol) was added dropwise over 2 h to a stirred solution of title compound of Step A (34.57 g, 149.6 mmol) and 4-dimethylaminopyridine (914 mg, 7.48 mmol) in dry tetrahydrofuran (450 mL) at room temperature under a nitrogen atmosphere. The reaction was allowed to stir at room temperature overnight. First, water was added to the reaction, and then the reaction mixture was poured into water. The mixture was saturated with sodium chloride and was extracted with ethyl acetate three times. The combined organic layers were dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give a brown oil. The brown oil was suspended in 1-chlorobutane. The resultant precipitate was filtered from this suspension to afford the title compound of Step B as a brown solid melting at 136°-138° C. (21.67 g, 46%). 1H NMR (CDCl3): δ2.35 (s,3H), 2.41 (s,3H), 3.63 (s,2H), 7.69 (s,2H), 9.6 (br s, 1H).

Workup

  1. extractionwas extracted with ethyl acetate three times
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customto give a brown oil
  6. filtrationThe resultant precipitate was filtered from this suspension

Sources & evidence

ORD record
ord-8b376187240b4ed782555b182275be4f
Source dataset
uspto-grants-1997_05
Patent number
US05633218

Reaction notes

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