Triethylamine → 4-Fluorobenzenesulfonic acid 2-(cyclopropanecarbonylamino)-benzothiazol-6-yl ester

HRID 1867958Notes

Reaction equation

HRID 1867958 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([CH:12]3[CH2:14][CH2:13]3)=[O:11])[S:8][C:4]=2[CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(N(CC)CC)C>CC(C)=O>[CH:12]1([C:10]([NH:9][C:7]2[S:8][C:4]3[CH:3]=[C:2]([O:1][S:24]([C:21]4[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=4)(=[O:26])=[O:25])[CH:16]=[CH:15][C:5]=3[N:6]=2)=[O:11])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 57980821N-(6-hydroxy-1,3-benzothiazol-2-yl)cyclopropanecarboxamide2×

Product 1

HCID 115239994-Fluorobenzenesulfonic acid 2-(cyclopropanecarbonylamino)-benzothiazol-6-yl esterYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of cyclopropanecarboxylic acid (6-hydroxybenzothiazol-2-yl)amide (intermediate 6) (1.81 g, 7.72 mmol), 4-fluorobenzenesulfonyl chloride (1.5 g, 7.72 mmol) and triethylamine (2.14 ml, 15.45 mmol) in 43 ml of acetone, in a 100 ml round-bottomed flask equipped with a magnetic bar, is stirred for 1 hour at room temperature. The precipitate obtained is filtered off and the filtrate is evaporated. The residue is washed with acetone and ethyl ether, to give 1.92 g of 4-fluorobenzenesulfonic acid 2-(cyclopropanecarbonylamino)-benzothiazol-6-yl ester (off-white powder) in a yield of 66%.

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered off
  3. customthe filtrate is evaporated
  4. washThe residue is washed with acetone and ethyl ether

Sources & evidence

ORD record
ord-2c269a36b60f40ecbd6537ddf59cb0a5
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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