Hydrochloric Acid → HCID 22388493, compound

HRID 1072860Notes

Reaction equation

HRID 1072860 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[CH2:4][NH:5][C:6]1[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9].CN(C)C1C=CC=CC=1.[C:34](Cl)(=[O:36])[CH3:35].Cl>C1(C)C=CC=CC=1>[C:34]([N:5]([CH2:4][C:3]1[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:2]=1[Cl:1])[C:6]1[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 6367Acetyl chlorideHCID 22388331HCID 22388331, compound

Product 1

HCID 22388493HCID 22388493, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of dimethyl 2-(2,4-dichlorobenzyl)aminoterephthalate (12.00 g), N,N-dimethylaniline (7.92 g) and acetyl chloride (5.5 ml) in toluene (140 ml) was heated at 50° C. for 15 hr. After cooling, ice and concentrated hydrochloric acid were added to acidify the reaction mixture and the toluene layer was separated. The toluene layer was washed successively with water and a saturated aqueous sodium hydrogencarbonate solution, dried over sodium sulfate and concentrated. The residue was crystallized from 2-propanol to give the objective compound (8.40 g) as white crystals.

Workup

  1. temperatureAfter cooling
  2. customthe toluene layer was separated
  3. washThe toluene layer was washed successively with water
  4. dry with materiala saturated aqueous sodium hydrogencarbonate solution, dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-d4643d172e0b401da27b8c5f18ad4fac
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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