Dimethylformamide → HCID 13314822, compound

HRID 1446869Notes

Reaction equation

HRID 1446869 reaction equation
[CH3:1][N:2]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:3]1[S:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1.Br[CH:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:1][N:2]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:15][CH:14]=1)[C:3]1[S:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 13314817HCID 13314817, compound

Product 1

HCID 13314822HCID 13314822, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-[N-methyl-N-(5-chloro-2-benzothiazolyl)amino]phenol (2.0 g), methyl 2-bromopropionate (1.16 g), potassium carbonate (1.05 g) and dimethylformamide was heated at a temperature of 100° C. for a period of 1 hr with vigorous stirring. After cooling the mixture was poured into water and the aqueous mixture was extracted with dichloromethane. The organic extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was recrystallised from methanol to give methyl 2-{4-[N-methyl-N-(5-chloro-2-benzothiazolyl)amino]phenoxy}propionate (1.55 g) as colourless crystals, mp 120° C.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionthe aqueous mixture was extracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe residue was recrystallised from methanol

Sources & evidence

ORD record
ord-6cce13a3376946508f2e843e8ff3c191
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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