Water → HCID 54195974, compound

HRID 371501Notes

Reaction equation

HRID 371501 reaction equation
[N:1]1([C:10]2[CH:11]=[C:12]([CH2:16]O)[CH:13]=[CH:14][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH2:18](N(CC)CC)C.C[S:26](Cl)(=[O:28])=[O:27].[OH2:30]>C(Cl)Cl>[CH3:18][O:30][S:26]([CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)[CH:11]=1)(=[O:28])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13324751HCID 13324751, compound

Product 1

HCID 54195974HCID 54195974, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 8.11 g (36 mmole) of 3-(1-indolinyl)benzenemethanol of Example 20b and 7.6 ml (54 mmole) of triethylamine in 35 ml of methylene chloride (CH2Cl2) was cooled to 0° C. and then treated dropwise with a solution of 3.1 ml (40 mmole) of methanesulfonyl chloride in 35 ml of CH2Cl2. Ten minutes after the addition, 150 ml of water was added. The organic layer was separated, washed twice with 150 ml of cold 2N-HCl, then with 150 ml of saturated NaHCO3, with 150 ml of brine, dried over Na2SO4 and concentrated in vacuo. This left 10.3 g (93.9% yield) of 3-(1-indolinyl)benzenemethanesulfonic acid methyl ester as an oil.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed twice with 150 ml of cold 2N-HCl
  4. dry with materialwith 150 ml of saturated NaHCO3, with 150 ml of brine, dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c4669fdeb0a4a3db87e4553f924deb8
Source dataset
uspto-grants-1985_07
Patent number
US04532333

Reaction notes

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