Benzoyl chloride → HCID 13651303, compound

HRID 1762286Notes

Reaction equation

HRID 1762286 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].C(N(CC)CC)C.CN(C)C(=O)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O.CO>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[O:12][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 31374DimethylacetamideHCID 38948482-Amino-4-chloro-5-nitrophenol

Product 1

HCID 13651303HCID 13651303, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

377 g (2 moles) of 2-amino-4-chloro-5-nitrophenol and 280 ml (2 moles) of triethylamine were added to 1 liter of N,N-dimethylacetoamide, followed by dropping 281 g (2 moles) of benzoyl chloride at about 50° C. in about 30 minutes. After continuing the agitation for further 30 minutes, 1 liter of methanol and 1 liter of water were added to the reaction solution. The resulting crystals were filtered and washed with 1 liter of methanol, thereby obtaining 547 g (yield 94%) of captioned benzoate compound. m.p. 207°-210° C., IR spectrum νC=0, 1725 cm-1.

Workup

  1. customat about 50° C.
  2. customin about 30 minutes
  3. customfor further 30 minutes
  4. filtrationThe resulting crystals were filtered
  5. washwashed with 1 liter of methanol

Sources & evidence

ORD record
ord-8b83d3e8428a4ecb9670e824a412b00f
Source dataset
uspto-grants-1989_05
Patent number
US04831152

Reaction notes

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