Triethylamine → HCID 23001840, compound

HRID 398084Notes

Reaction equation

HRID 398084 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[C:20]([CH3:26])[CH:19]=2)=[C:11]([CH:16]=1)[CH2:12][N:13]([CH3:15])[CH3:14].CCN(CC)CC>C(Cl)Cl.CCOC(C)=O>[CH3:15][N:13]([CH2:12][C:11]1[CH:16]=[C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:8]=[CH:9][C:10]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[C:20]([CH3:26])[CH:19]=1)[CH3:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23001836HCID 23001836, compound

Product 1

HCID 23001840HCID 23001840, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (371 μL, 4.79 mmol) was added to a solution of the aniline of Example 103 (725 mg, 2.4 mmol) and Et3N (1 mL, 7.17 mmol) in DCM (10 mL) at 0° C. After stirring at 0° C. for 1 h the reaction was allowed to warm to room temperature before the solvent was removed in vacuo. 2M NaOH (10 mL) was added to the residue and the mixture was stirred overnight. The resulting clear solution was neutralised by the addition of sat aq NH4Cl and extracted with DCM (2×30 mL). The combined organic layers were dried (MgSO4) and evaporated to give an oil. This was taken up in EtOAc (10 mL), the HCl salt was precipitated by the addition of 1M ethereal HCl and the product (669 mg, 67%) was collected by filtration; δH (d6-DMSO, 400 MHz) 2.23 (3H, s), 2.42 (3H, s), 2.75 (6H, s), 3.04 (3H, s), 4.38 (2H, s), 6.84 (1H, d), 6.93 (1H, d), 6.98 (1H, s), 7.17-7.25 (2H, m), 7.50 (1H, s); MS m/z (ES+) 381 (MH+).

Workup

  1. temperatureto warm to room temperature before the solvent
  2. customwas removed in vacuo
  3. addition2M NaOH (10 mL) was added to the residue
  4. stirringthe mixture was stirred overnight
  5. additionThe resulting clear solution was neutralised by the addition of sat aq NH4Cl
  6. extractionextracted with DCM (2×30 mL)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. customevaporated
  9. customto give an oil
  10. customthe HCl salt was precipitated by the addition of 1M ethereal HCl
  11. filtrationthe product (669 mg, 67%) was collected by filtration

Sources & evidence

ORD record
ord-123111b57e3844f582920aadc96f1ae9
Source dataset
uspto-grants-2003_08
Patent number
US06610747B2

Reaction notes

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