Water → HCID 19001528, compound

HRID 2259642Notes

Reaction equation

HRID 2259642 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:10]([C:13]1[CH:23]=[CH:22][C:16]2[N:17]=[C:18]([CH2:20][OH:21])[S:19][C:15]=2[CH:14]=1)([O-:12])=[O:11].C(N(CC)CC)C.O>O1CCCC1>[N+:10]([C:13]1[CH:23]=[CH:22][C:16]2[N:17]=[C:18]([CH2:20][O:21][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[S:19][C:15]=2[CH:14]=1)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 19001526HCID 19001526, compound

Product 1

HCID 19001528HCID 19001528, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9 ml of benzoyl chloride was added dropwise to a solution of 15 g of the 6-nitro-2-hydroxymethylbenzothiazole obtained in the Preparation Example 2 and 11 ml of triethylamine in tetrahydrofuran at 10° C. The reaction mixture was stirred at room temperature for 1 h and water was added thereto. After extraction with ethyl acetate, the extract was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent: dichloromethanol/methanol) to give 10 g of the titled compound.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. dry with materialthe extract was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (solvent: dichloromethanol/methanol)

Sources & evidence

ORD record
ord-9a577f7a783f4d2095de25a6bbb2da0e
Source dataset
uspto-grants-1995_12
Patent number
US05475014

Reaction notes

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