Ammonia → 2-amino-2,3-dihydro-1H-indene-5-sulfonamide

HRID 1701339Notes

Reaction equation

HRID 1701339 reaction equation
C(NC1CC2C(=CC=CC=2)C1)(=O)C.ClS(O)(=O)=O.C([NH:22][CH:23]1[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([S:32](=[O:35])(=[O:34])[NH2:33])[CH:29]=2)[CH2:24]1)(=O)C.N>C1COCC1.O>[S:32]([C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[CH2:24][CH:23]([NH2:22])[CH2:31]2)(=[O:34])(=[O:35])[NH2:33]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 24638Chlorosulfonic acidHCID 11414131N-(5-sulfamoyl-2,3-dihydro-1H-inden-2-yl)acetamideHCID 12452137N-(2,3-Dihydro-1H-inden-2-yl)acetamide

Product 1

HCID 203478462-amino-2,3-dihydro-1H-indene-5-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

1.75 g. of N-acetyl-2-indanamine (0.01 mole) was added to 20 g. of chlorosulfonic acid (0.18 mole), stirred at -60° C. and allowed to warm to 25° C. The mixture was stirred until the reaction was complete, poured into cold water and extracted with ethyl acetate. Evaporation gave the crude N-acetyl-5-chlorosulfonyl-2-indanamine which was converted to N-acetyl-5-sulfamyl-2-indanamine with ammonia in THF. The N-acetyl sulfonamide was purified by recrystallization from water, m.p. 237°-239° C. and hydrolyzed in refluxing 10% hydrochloric acid to give 5-sulfamyl-2-indanamine which was recrystallized from methanol-ether, m.p. 261°-264° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customEvaporation
  3. customgave the crude N-acetyl-5-chlorosulfonyl-2-indanamine which
  4. customThe N-acetyl sulfonamide was purified by recrystallization from water, m.p. 237°-239° C.
  5. temperaturehydrolyzed in refluxing 10% hydrochloric acid

Sources & evidence

ORD record
ord-84ade9db62e240b6ba4bf996431d70f0
Source dataset
uspto-grants-1980_03
Patent number
US04192888

Reaction notes

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