Water → HCID 15746687, compound

HRID 1109715Notes

Reaction equation

HRID 1109715 reaction equation
[F:1][C:2]1[C:14]([NH:15][C:16]([O:18][CH:19]([C:23]([O:25]C)=O)[C:20]([CH3:22])=[CH2:21])=[O:17])=[CH:13][C:5]2[N:6]([CH2:10][C:11]#[CH:12])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.S1(=O)C2C=CC=CC=2N=C1.O>C1(C)C=CC=CC=1.C[O-].[Na+]>[F:1][C:2]1[C:14]([N:15]2[C:23](=[O:25])[C:19](=[C:20]([CH3:22])[CH3:21])[O:18][C:16]2=[O:17])=[CH:13][C:5]2[N:6]([CH2:10][C:11]#[CH:12])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 15746686HCID 15746686, compoundHCID 53400715Benzothiazolinone

Product 1

HCID 15746687HCID 15746687, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 10942334Sodium MethoxideSolvent

Procedure

To a solution of 6-fluoro-5-(1-methoxycarbonyl-2-methyl-2-propenyloxycarbonylamino)-3-propargyl-2(3H)-benzothiazolone (10 g) in toluene (100 g), sodium methylate was added in an amount of 0.05 equivalent to one equivalent of the benzothiazolone. The resulting mixture was refluxed for 3 hours, cooled to room temperature, combined with water and extracted with ethyl acetate. The organic layer was purified by silica gel column chromatography to give Compound No. 40 (6.8 g).

Workup

  1. temperatureThe resulting mixture was refluxed for 3 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was purified by silica gel column chromatography
  4. customto give Compound No

Sources & evidence

ORD record
ord-6364b5ffc32d452bb92a59c7e2de47f0
Source dataset
uspto-grants-1994_06
Patent number
US05322835

Reaction notes

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