Water → HCID 86049094, compound

HRID 2235514Notes

Reaction equation

HRID 2235514 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([CH3:28])[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[NH:13][C:14]1[S:15][C:16]2[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([CH2:26]O)=[CH:19][C:17]=2[N:18]=1.O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Cl:3][CH2:26][C:20]1[CH:21]=[C:22]([N+:23]([O-:25])=[O:24])[C:16]2[S:15][C:14]([NH:13][C:6]3[C:7]([CH3:12])=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=3[CH3:28])=[N:18][C:17]=2[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 86049092HCID 86049092, compound

Product 1

HCID 86049094HCID 86049094, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Thionyl chloride (0.191 ml, 2.62 mmol) was added to a solution of (2-mesitylamino-7-nitro-1,3-benzothiazol-5-yl)methanol (180 mg, 0.524 mmol) in chloroform. The mixture was stirred at room temperature for 18 h and at 60° C. for 24h. The mixture was poured into water and neutralized with saturated NaHCO3 solution. The aqueous solution was extracted with AcOEt. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by chromatography eluting with 20% AcOEt in n-hexane to afford 122 mg of the title compound.

Workup

  1. extractionThe aqueous solution was extracted with AcOEt
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by chromatography
  6. washeluting with 20% AcOEt in n-hexane

Sources & evidence

ORD record
ord-70abf35db13b443aa8be8708dc685a0d
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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