Dicyclohexano-18-crown-6 → HCID 15908227, compound

HRID 988083Notes

Reaction equation

HRID 988083 reaction equation
[O:1]=[S:2]1(=[O:16])[C:7]2[CH:8]=[C:9]([OH:12])[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:13][CH2:14][CH2:15][CH:4]2[NH:3]1.[C:17](OCCl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19].C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3>C(#N)C>[C:17]([O:12][C:9]1[CH:10]=[CH:11][C:6]2[N:5]3[CH2:13][CH2:14][CH2:15][CH:4]3[NH:3][S:2](=[O:1])(=[O:16])[C:7]=2[CH:8]=1)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 85955Dicyclohexano-18-crown-6HCID 87885Chloromethyl pivalateHCID 98135182,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-ol 5,5-dioxide

Product 1

HCID 15908227HCID 15908227, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.66 mmol of the compound of Example 1 in 40 ml of acetonitrile are stirred overnight at room temperature in the presence of 3.33 mmol of chloromethyl pivalate and a catalytic amount of dicyclohexyl-18-crown-6. The suspension is filtered and the filtrate is evaporated to dryness. The residue is taken up in dichloromethane and the organic phase is washed with a 1N hydrochloric acid solution and then with an aqueous saturated sodium chloride solution. After drying and evaporation, the resulting oily residue is crystallised from a mixture of ether/cyclohexane to yield the expected product.

Workup

  1. filtrationThe suspension is filtered
  2. customthe filtrate is evaporated to dryness
  3. washthe organic phase is washed with a 1N hydrochloric acid solution
  4. customAfter drying
  5. customevaporation
  6. customthe resulting oily residue is crystallised from a mixture of ether/cyclohexane

Sources & evidence

ORD record
ord-b89ffd9b7a6542fca204c96f1421fafe
Source dataset
uspto-grants-2003_10
Patent number
US06635635B2

Reaction notes

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