Water → 3,3-Dimethyl-1-methylsulfonylaminoindan

HRID 850019Notes

Reaction equation

HRID 850019 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:17])([CH3:16])[CH2:8]1.C(N(CC)CC)C.O>C1COCC1>[CH3:16][C:9]1([CH3:17])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 230089363,3-dimethyl-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 193659003,3-Dimethyl-1-methylsulfonylaminoindanYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

with ice-cooling, 4.0 g (34.7 mmol) of methanesulfonyl chloride were added dropwise to a solution of 5.1 g (31.6 mmol) of 1-amino-3,3-dimethylindan and 12.8 g (126.4 mmol) of triethylamine in 100 ml of THF. After 2 h at RT, 100 ml of water were added, the reaction mixture was concentrated to about 50 ml and admixed with 100 ml of water and the precipitate was filtered off with suction, rinsed with water and dried under reduced pressure. This procedure gave 6.7 g of 3,3-dimethyl-1-methylsulfonylaminoindan; m.p. 117-119° C.

Workup

  1. temperaturewith ice-cooling
  2. concentrationthe reaction mixture was concentrated to about 50 ml
  3. filtrationthe precipitate was filtered off with suction
  4. washrinsed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-50dba670c6394793ac5b932f7d20e6f9
Source dataset
uspto-grants-2000_01
Patent number
US06015822

Reaction notes

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