Acetyl chloride → 1353777-30-6

HRID 1470739Notes

Reaction equation

HRID 1470739 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][C:3]=1[OH:10].[CH2:11](N(CC)CC)[CH3:12].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(Cl)(=O)C>C1(C)C(C)=CC=CC=1>[Br:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]2[N:1]=[C:11]([CH3:12])[O:10][C:3]=2[CH:4]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67125436Phenol, 2-amino-5-bromo-3-methyl-

Product 1

HCID 679709581353777-30-6

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To 1.5 g (7.42 mmol) 2-amino-5-bromo-3-methyl-phenol in 30 mL xylene is added 1.15 mL (8.19 mmol) triethylamine, 0.68 g (2.70 mmol pyridinium p-toluenesulfonate and 0.55 mL (7.74 mmol) acetyl chloride. The mixture is refluxed for 3 d. Subsequently the solvent is removed in vacuo, and the residue is treated with 50 mL ethylacetate. The mixture is extracted twice with water. The combined aq. layers are extracted with ethylacetate. The combines organic layers are dried and concentrated to yield the desired product.

Workup

  1. temperatureThe mixture is refluxed for 3 d
  2. customSubsequently the solvent is removed in vacuo
  3. additionthe residue is treated with 50 mL ethylacetate
  4. extractionThe mixture is extracted twice with water
  5. extractionThe combined aq. layers are extracted with ethylacetate
  6. customThe combines organic layers are dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-90c8d6bb65b141668545b47d8ff92f6e
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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