Boron tribromide → HCID 18412424, compound

HRID 50209Notes

Reaction equation

HRID 50209 reaction equation
[C:1]1([N:7]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:8]([C:10]2[CH:11]=[CH:12][C:13]3[S:17][C:16]([CH2:18]OC)=[N:15][C:14]=3[CH:21]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)[Br:30]>ClCCl>[C:1]1([N:7]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:8]([C:10]2[CH:11]=[CH:12][C:13]3[S:17][C:16]([CH2:18][Br:30])=[N:15][C:14]=3[CH:21]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 184125442-methoxymethylbenzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

Product 1

HCID 18412424HCID 18412424, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2.05 g (5.14 mmol) of 2-methoxymethylbenzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide and 5.7 mL (5.7 mmol) of a 1M solution of boron tribromide in dichloromethane was dissolved in a further 60 mL of dichloromethane and stirred for 16 hours at room temperature. Then the mixture was washed with 40 mL of saturated sodium hydrogen carbonate solution, the organic phase was dried with sodium sulfate, and the solvent was distilled off. The crude 2-bromomethylbenzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide thus obtained (2.4 g) was taken up in 5.0 mL of N,N-diisopropylethylamine and mixed with 0.64 g (5.4 mmol) of 4-aminobenzonitrile. After 1 hour's heating to 130° C., the solvent was distilled off in vacuo and the crude product obtained was purified by flash chromatography (silica gel; gradient: ethyl acetate/petroleum ether=1:3 to 1:1), whilst an orange foam was obtained when the eluates were evaporated down. Yield: 1.1 g (44% of theory); Rf value: 0.35 (silica gel; ethyl acetate/petroleum ether=7:3).

Workup

  1. washThen the mixture was washed with 40 mL of saturated sodium hydrogen carbonate solution
  2. dry with materialthe organic phase was dried with sodium sulfate
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-cfcf7bb1b25e486ba2ce305b1478a146
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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