Water → HCID 59402700, compound

HRID 538605Notes

Reaction equation

HRID 538605 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]2[N:9]=[C:10]([CH2:12]O)[S:11][C:7]=2[CH:6]=1)=[O:4].P(Br)(Br)[Br:17].O>C1(C)C=CC=CC=1.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]2[N:9]=[C:10]([CH2:12][Br:17])[S:11][C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 59402886HCID 59402886, compound

Product 1

HCID 59402700HCID 59402700, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-Hydroxymethyl-benzothiazole-6-carboxylic acid methyl ester (0.08 g, 0.40 mmol) in 5 ml of toluene and 1 ml of DMF was added PBr3 (0.06 ml, 0.60 mmol). The reaction mixture was heated at 120° C. for 20 min under nitrogen atmosphere. After the completion of the reaction mixture (TLC monitoring), water (25 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated to get the desired product (0.044 g, 36%).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organics was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2c909ebcd4a340e6b68c72d7e0c11aeb
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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