Dimethylformamide → 7-Acetyl-4-(benzyloxy)-1,3-benzothiazol-2(3H)-one

HRID 749240Notes

Reaction equation

HRID 749240 reaction equation
[C:1]([C:4]1[C:12]2[S:11][C:10](=[O:13])[NH:9][C:8]=2[C:7]([OH:14])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CN(C=O)C.C(N(CC)C(C)C)(C)C.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1.O>[C:1]([C:4]1[C:12]2[S:11][C:10](=[O:13])[NH:9][C:8]=2[C:7]([O:14][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 450769877-Acetyl-4-hydroxybenzo[d]thiazol-2(3H)-one

Product 1

HCID 693219837-Acetyl-4-(benzyloxy)-1,3-benzothiazol-2(3H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-acetyl-4-hydroxy-1,3-benzothiazol-2(3H)-one (153 mg), in dry THF (3 ml) and dry DMF (0.5 ml) under nitrogen, was added N,N-diisopropylethylamine (0.13 ml) and benzyl bromide (0.09 ml), and the mixture stirred for 72 h. Water (10 ml) was added and the mixture extracted with ethyl acetate. The organic phases were combined, washed with brine, dried (MgSO4), and evaporated in vacuo. The residue was purified on a 5 g silica SPE cartridge, eluting with a stepped gradient of 10% to 50% ethyl acetate-cyclohexane mixtures, to give the title compound (68 mg). LCMS RT=3.14 min.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was purified on a 5 g silica SPE cartridge
  6. washeluting with a stepped gradient of 10% to 50% ethyl acetate-cyclohexane mixtures

Sources & evidence

ORD record
ord-b853c45fcafa4252a8f6ce0233d3b0e2
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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