Chloride → HCID 10517794, compound

HRID 1834543Notes

Reaction equation

HRID 1834543 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Cl:13])=[CH:6][C:4]=1[NH2:5].[Cl-:14]>C1C=CC=CC=1.N1C=CC=CC=1.O>[Cl:14][CH2:6][CH2:4][C:3]([NH:5][C:4]1[CH:6]=[C:7]([Cl:13])[C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:3]=1[O:2][CH3:1])=[O:2]

Participants

6

Reactant 2

HCID 312ChlorideHCID 804105-Chloro-4-nitro-o-anisidine

Product 1

HCID 10517794HCID 10517794, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

17.2 g of 2 -methoxy 4 -nitro 5 -chloroaniline dissolved in 150 ml benzene are added with 11.1 g of β chloropropionly chloride dissolved in 40 ml benzene and 2 ml pyridine. The reaction mixture is kept under stirring at room temperature for two hours then diluted with 250 ml water. The benzenic phase is separated while the aqueous phase is extracted twice with benzene. The benzenic solutions are united, washed with 2N hydrochloric acid then with water, dried on sodium sulphate, filtered and evaporated to dryness. The dry residue is recristallised from isopropyl ether and 21.1 g of 1(β chloropropionylamino) 2 -methoxy 4 -nitro 5 -chlorobenzene are recovered (yield 40-50%). It melts at 101°-110° (dec)

Workup

  1. customThe benzenic phase is separated while the aqueous phase
  2. extractionis extracted twice with benzene
  3. washwashed with 2N hydrochloric acid
  4. dry with materialwith water, dried on sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customare recovered (yield 40-50%)

Sources & evidence

ORD record
ord-57e88a48a0fb4bb88ad1e1945fc9ea5f
Source dataset
uspto-grants-1978_01
Patent number
US04070485

Reaction notes

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