Sodium hydride → HCID 9853605, compound

HRID 1358765Notes

Reaction equation

HRID 1358765 reaction equation
[OH:1][C:2]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([OH:18])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].Cl[C:22]1[CH:27]=[CH:26][C:25]([S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29])=[CH:24][C:23]=1[N+:35]([O-:37])=[O:36]>O1CCCC1.C(Cl)(Cl)Cl.C(O)(C)C>[CH2:16]([O:15][C:13](=[O:14])[C:11]1[CH:12]=[C:2]([O:1][C:22]2[CH:27]=[CH:26][C:25]([S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29])=[CH:24][C:23]=2[N+:35]([O-:37])=[O:36])[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:9][C:10]=1[O:18][C:22]1[CH:27]=[CH:26][C:25]([S:28]([C:31]([F:33])([F:34])[F:32])(=[O:30])=[O:29])=[CH:24][C:23]=1[N+:35]([O-:37])=[O:36])[CH3:17]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79980Diethyl 2,5-dihydroxyterephthalateHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzene4×

Product 1

HCID 9853605HCID 9853605, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

A mixture of diethyl 2,5-dihydroxyterephthalate (127 mg, 0.5 mmol) and sodium hydride (60%, 20 mg) in tetrahydrofuran (1.5 mL) was stirred at room temperature for 30 minutes followed by the addition of 1-chloro-2-nitro-4-trifluoromethanesulfonyl-benzene (75 mg, 0.26 mmol). After 45 mintues, more 1-chloro-2-nitro-4-trifluoromethanesulfonyl-benzene (63 mg, 0.22 mmol) was added. Tetrahydrofuran (1 mL) was added after each addition of 1-chloro-2-nitro-4-trifluoromethanesulfonyl-benzene. After 18 hours at room temperature, more 1-chloro-2-nitro-4-trifluoromethanesulfonyl-benzene (75 mg) was added and the temperature was increased to 60° C. for 2 hours. The reaction was diluted with chloroform/isopropanol, washed with brine and purified on silica gel to give the title compound. 1H NMR (360 MHz, DMSO-d6) δ 8.82 (d, J=2.2 Hz, 2H), 8.27 (dd, 2H), 8.18 (s, 2H), 7.48 (d, J=9 Hz, 2H), 4.15 (q, J=6.8 Hz, 4H), 0.98 (t, J=6.8 Hz, 6H).

Workup

  1. waitAfter 18 hours at room temperature
  2. temperaturethe temperature was increased to 60° C. for 2 hours
  3. washwashed with brine
  4. custompurified on silica gel

Sources & evidence

ORD record
ord-d129a262805f4fb783827dd019ca834a
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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