4-Toluenesulfonyl chloride → HCID 59276512, compound

HRID 2070865Notes

Reaction equation

HRID 2070865 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:8]([S:9]([C:12]2[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:7]2[CH:19]=[CH:20][C:21]([N+]([O-])=O)=[CH:22][C:6]=2[N:5]=1.COCC1NC2C=CC([N+]([O-])=O)=CC=2[N:30]=1.CC1C=CC(S(Cl)(=O)=O)=CC=1.CC(C)([O-])C.[Na+]>O1CCCC1.C(OCC)(=O)C.O>[CH3:1][O:2][CH2:3][C:4]1[N:8]([S:9]([C:12]2[CH:13]=[CH:14][C:15]([CH3:16])=[CH:17][CH:18]=2)(=[O:11])=[O:10])[C:7]2[CH:19]=[C:20]([NH2:30])[CH:21]=[CH:22][C:6]=2[N:5]=1

Participants

8

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 23676156Sodium t-butoxideHCID 68588158HCID 68588158, compoundHCID 178494650HCID 178494650, compound

Product 1

HCID 59276512HCID 59276512, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(Methoxymethyl)-5-nitro-1-tosyl-1H-benzo[d]imidazole. 2-(Methoxymethyl)-5-nitro-1H-benzo[d]imidazole (1.23 g, 5.94 mmol) and 4-methylbenzene-1-sulfonyl chloride (1.358 g, 7.12 mmol) were dissolved in tetrahydrofuran (50 mL) and sodium tert-butoxide (1.141 g, 11.87 mmol) was added. The mixture was stirred at room temperature for 16 h. The reaction mixture was poured into a separatory funnel containing water and 50% ethyl acetate. The organic layer was concentrated on a rotary evaporator nearly to dryness and purified on silica column eluting with 0-50% ethyl acetate in hexane. The fractions containing product were concentrated on a rotary evaporator to give the desired product as white solid (0.9 g, 42% yield). MS (ESI) m/z 362.3 [M+1]+.

Workup

  1. additionThe reaction mixture was poured into a separatory funnel
  2. concentrationThe organic layer was concentrated on a rotary evaporator nearly to dryness
  3. custompurified on silica column
  4. washeluting with 0-50% ethyl acetate in hexane
  5. additionThe fractions containing product
  6. concentrationwere concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-2ab3cc426fc84af8b7a43b6805d93537
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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