Diethyl Ether → 4-Methoxy-N-hydroxybenzenecarboximidoyl chloride

HRID 1576979Notes

Reaction equation

HRID 1576979 reaction equation
CO[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH:5]=[N:6][OH:7].N([Cl:14])=O.CC[O:17][CH2:18]C>>[CH3:18][O:17][C:10]1[CH:11]=[CH:3][C:4]([C:5]([Cl:14])=[N:6][OH:7])=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 17601Nitrosyl chlorideHCID 141489N-[(2-methoxyphenyl)methylidene]hydroxylamine

Product 1

HCID 27633714-Methoxy-N-hydroxybenzenecarboximidoyl chloride

Procedure

By the method of Example I-B, 43.6 g of methoxybenzaldoxime in 510 ml of ether was treated with 21.0 g of nitrosyl chloride. After removal of the ether, the product oil was triturated with benzene-hexane and crystallized from benzene-hexane. The filtrate from the crystallization was concentrated to about one-third of its original volume and placed in the refrigerator. The solid which formed and the first crop of crystals were combined and recrystallized from hexane-ether to give 13.2 g of 4-methoxybenzohydroximoyl chloride, m.p. 87.5°-89.5°. The ir spectrum was consistent with the assigned structure.

Workup

  1. customAfter removal of the ether
  2. customthe product oil was triturated with benzene-hexane
  3. customcrystallized from benzene-hexane
  4. customThe filtrate from the crystallization
  5. concentrationwas concentrated to about one-third of its original volume
  6. customThe solid which formed
  7. customrecrystallized from hexane-ether

Sources & evidence

ORD record
ord-08e2dab292ba4230a9d6de8de53e9ee8
Source dataset
uspto-grants-1976_09
Patent number
US03983246

Reaction notes

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