Tetrahydrofuran → HCID 17878496, compound

HRID 2395269Notes

Reaction equation

HRID 2395269 reaction equation
O1CCCC1.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]=[C:17]=[O:18])(=[O:15])=[O:14])=[CH:9][CH:8]=1.[NH2:19][C:20]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:21]=1[C:22]([OH:24])=O.C1N=CN(C(N2C=NC=C2)=O)C=1>O>[Cl:29][C:27]1[CH:28]=[C:20]2[C:21]([C:22](=[O:24])[N:16]([S:13]([C:10]3[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=3)(=[O:14])=[O:15])[C:17](=[O:18])[NH:19]2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 666462-Amino-4-chlorobenzoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 1385874-Chlorobenzenesulfonyl isocyanate

Product 1

HCID 17878496HCID 17878496, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following Synthesis Method (A), into 200 ml of anhydrous tetrahydrofuran (hereinafter referred to as THF) was dissolved 4.90 g (22.5 mmol) of 4-chlorobenzenesulfonylisocyanate, then 3.51 g (20.5 mmol) of 2-amino-4-chlorobenzoic acid was added and the mixture was stirred at room temperature for two hours. The reaction solution was cooled by ice water, then 3.98 g (24.55 mmol) of CDI was added and the mixture was stirred under ice cooling for 30 minutes. An excess amount of water was poured into the reaction solution, then the precipitated crystal was obtained by filtration and the obtained crystal was washed by water, then was washed by ethyl acetate to obtain 5.03 g of the above-identified compound (yield 66.5%). Properties: colorless crystal, Melting point: 286°-287° C., PMR (δppm, DMSO-d6): 7.12 (1H,s), 7.23 (1H,d), 7.26 (2H,d), 7.86 (1H,d), 8.17 (2H,d), 11.71 (1H,br).

Workup

  1. customSynthesis Method (A)
  2. stirringthe mixture was stirred under ice cooling for 30 minutes
  3. customthe precipitated crystal was obtained by filtration
  4. washthe obtained crystal was washed by water
  5. washwas washed by ethyl acetate

Sources & evidence

ORD record
ord-dcea11a26f374f53a9a61296c7c5486f
Source dataset
uspto-grants-1998_09
Patent number
US05814631

Reaction notes

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