2-Chlorobenzoic Acid → HCID 21189417, compound

HRID 1068554Notes

Reaction equation

HRID 1068554 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[Cl:11][C:12]1[CH:24]=[C:23]([Cl:25])[C:22]([S:26](=[O:29])(=[O:28])[NH2:27])=[CH:21][C:13]=1[C:14]([NH:16][CH2:17][CH2:18][O:19][CH3:20])=[O:15].C1CCN2C(=NCCC2)CC1>O1CCCC1>[Cl:11][C:12]1[CH:24]=[C:23]([Cl:25])[C:22]([S:26](=[O:28])(=[O:29])[NH:27][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[Cl:1])=[CH:21][C:13]=1[C:14]([NH:16][CH2:17][CH2:18][O:19][CH3:20])=[O:15]

Participants

5

Reactant 3

HCID 83742-Chlorobenzoic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21189414HCID 21189414, compound

Product 1

HCID 21189417HCID 21189417, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At room temperature, 1.0 g (6.1 mmol) of 2-chlorobenzoic acid are dissolved in 120 ml of tetrahydrofuran and mixed with 1.0 g (6.1 mmol) of N,N′-carbonyldiimidazole. After 30 minutes at room temperature and a further 30 minutes at reflux temperature, 2.0 g (6.1 mmol) of 2,4-dichloro-N-(2-methoxyethyl)-5-sulfamoylbenzamide are added at reflux temperature. After 10 minutes, 0.9 g (6.1 mmol) of 1,5-diazabicyclo[5.4.0]-5-undecene are added and the mixture is kept at reflux temperature for a further 3 hours. The mixture is subsequently evaporated to dryness, the residue is taken up in 60 ml of acetonitrile and the solution is poured into 60 ml of water. The solution is acidified to pH 1 using 2N HCI and the precipitate is separated off, washed with water and dried.

Workup

  1. additionare added
  2. temperatureat reflux temperature
  3. waitAfter 10 minutes
  4. temperatureat reflux temperature for a further 3 hours
  5. customThe mixture is subsequently evaporated to dryness
  6. additionthe solution is poured into 60 ml of water
  7. customthe precipitate is separated off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-2d4bcc29822847879dcc0d706574dfa9
Source dataset
uspto-grants-2001_06
Patent number
US06251827B1

Reaction notes

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