Ammonia → HCID 178492429, compound

HRID 2075946Notes

Reaction equation

HRID 2075946 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][C:12]([C:13](Cl)=[N:14][OH:15])=[C:11]([I:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:23](C)C=O.N.C(OCC)(=O)C>O>[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][C:12]([C:13]([NH:14][OH:15])=[NH:23])=[C:11]([I:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 866472264-benzyloxy-N-hydroxy-2-iodo-5-methoxy-benzimidoylchloride

Product 1

HCID 178492429HCID 178492429, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 4-benzyloxy-N-hydroxy-2-iodo-5-methoxy-benzimidoylchloride and N,N-dimethylformamide (110 mL) was added a 28% ammonia in water (12 mL) under ice-bath cooling. After stirring for 3 hours under ice-bath cooling, water and ethyl acetate were added to the mixture. The separated organic layer was washed with water and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with hexane:diethyl ether=1:4 to give the title compound (9.3 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. washThe separated organic layer was washed with water and brine successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-0aa487be90be4afebf7bf65fe3b0e39d
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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