Water → HCID 18703986, compound

HRID 2288064Notes

Reaction equation

HRID 2288064 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[NH2:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>C1COCC1>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[NH:14][S:23]([CH3:22])(=[O:25])=[O:24])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 121368527-nitro-1,2,3,4-tetrahydro-1-naphthalenamine

Product 1

HCID 18703986HCID 18703986, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.0 g (10.4 mmol) of 7-nitro-1,2,3,4-tetrahydro-1-naphthylamine in 35 ml of THF was treated with ice-cooling with 4.2 g (41.6 mmol) of triethylamine and 1.3 g (11.4 mmol) of methanesulfonyl chloride and then stirred at RT for 2 hrs. After addition of 20 ml of water, the mixture was concentrated in vacuo down to a 10 ml residue, then treated with a further 20 ml of water, and the precipitated product was filtered off with suction. After drying in vacuo, 2.5 g of N-(7-nitro-1,2,3,4-tetrahydronaphthalen-1-yl)methanesulfonamide were obtained; m.p. 150-152° C.

Workup

  1. concentrationthe mixture was concentrated in vacuo down to a 10 ml residue
  2. additiontreated with a further 20 ml of water
  3. filtrationthe precipitated product was filtered off with suction
  4. customAfter drying in vacuo

Sources & evidence

ORD record
ord-010ab8b8d2ea465cb9c91e67d3307428
Source dataset
uspto-grants-2000_07
Patent number
US06087399

Reaction notes

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