Triethylamine → 1-(Methanesulfonylpropyl)-indole-3-acetamide

HRID 1604062Notes

Reaction equation

HRID 1604062 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].O[CH:7]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][C:20]([NH2:22])=[O:21])=[CH:11]1)[CH2:8][CH3:9].C(N(CC)CC)C.[NH4+].[Cl-]>C(Cl)Cl.[Cl-].[Na+].O.O>[CH3:1][S:2]([CH2:9][CH2:8][CH2:7][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][C:20]([NH2:22])=[O:21])=[CH:11]1)(=[O:4])=[O:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 232889591-(1-Hydroxypropyl)-indole-3-acetamide

Product 1

HCID 542382211-(Methanesulfonylpropyl)-indole-3-acetamideYield 74.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Methanesulfonyl chloride (0.67 mL, 14.5 mmol) was added dropwise to a 0°-5° C. solution of 1-(1-hydroxypropyl)-indole-3-acetamide (1.68 g, 7.23 mmol) and triethylamine (1.41 mL, 10.1 mmol) in CH2Cl2 (20 mL) under N2. The reaction was stirred 30 minutes in the ice bath and then the reaction was worked up extractively using CH2Cl2 (200 mL), water (100 mL), aqueous saturated NH4Cl (100 mL) and brine (50 ml), and the organic layer dried (MgSO4) and the solvent removed in vacuo to give a solid that was triturated in THF (15 mL) and filtered to give 1.58 g (71%) of the above titled compound after drying. NMR. MS (FD) m/z=310 (M+, 100%). Analytical calculated for C14H18N2O3S C, 54.18; H, 5.85; N, 9.03. Found C, 54.64; H, 5.98; N, 8.97.

Workup

  1. dry with materialthe organic layer dried (MgSO4)
  2. customthe solvent removed in vacuo
  3. customto give a solid
  4. customthat was triturated in THF (15 mL)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-f2a54f080cdf49cdbb3d9560e5f91f97
Source dataset
uspto-grants-1999_11
Patent number
US05990319

Reaction notes

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