Water → HCID 67312845, compound

HRID 339535Notes

Reaction equation

HRID 339535 reaction equation
[OH:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:16][C:17]4[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:18]=4[N:19]=3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.Cl[CH:29]([OH:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[OH:31][CH2:29][CH2:30][O:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:16][C:17]4[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:18]=4[N:19]=3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 126390351-Chloroethan-1-olHCID 67312510HCID 67312510, compound

Product 1

HCID 67312845HCID 67312845, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-hydroxy-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide (0.20 g, 0.53 mmol), chloroethanol (0.064 g, 0.80 mmol) and potassium carbonate (0.26 g, 1.86 mmol) was heated at 100° C. in dry DMF (10 ml) for 18 h. On cooling to room temperature, water (30 ml) was added and the reaction mixture was extracted with EtOAc (7×40 ml). The combined organic extracts were washed with brine (80 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give the title compound (0.17 g, 76%) as a colourless solid.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc (7×40 ml)
  2. washThe combined organic extracts were washed with brine (80 ml)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fc7bf1e27ae948ebab486fcca361de5b
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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