Water → HCID 22283318, compound

HRID 1060296Notes

Reaction equation

HRID 1060296 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13](=[O:15])[OH:14])[S:11][C:7]=2[C:6]([CH:16]=[CH2:17])=[CH:5][CH:4]=1.[OH2:18].C1C(=O)N([Br:26])C(=O)C1>C1COCC1>[Br:26][CH2:17][CH:16]([C:6]1[C:7]2[S:11][C:10]([NH:12][C:13](=[O:14])[OH:15])=[N:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[OH:18]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 22283075HCID 22283075, compound

Product 1

HCID 22283318HCID 22283318, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 g of (4-methoxy-7-vinyl-benzothiazol-2-yl)-carbamic acid methyll ester (0.0057 Mol), dissolved in THF (60 ml) were treated with H2O (6 ml) and 1.0 g of NBS (0.006 Mol) at room temperature for 15 min. Then the solvent was removed, the residue taken up in H2O (30 ml) and extracted four times with ethyl acetate (50 ml). The combined organic phases were washed with brine and dried over MgSO4. After evaporation the crude product was subjected to column chromatography (silicagel, ethyl acetate). The title compound was obtained as a white solid (78%), F.p.: 150-155° C.

Workup

  1. customThen the solvent was removed
  2. extractionextracted four times with ethyl acetate (50 ml)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. customAfter evaporation the crude product

Sources & evidence

ORD record
ord-d961e430973c424fb9414fa216d999a9
Source dataset
uspto-grants-2003_02
Patent number
US06521754B2

Reaction notes

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