Methane → HCID 70523752, compound

HRID 904857Notes

Reaction equation

HRID 904857 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:10]=[C:9]([Cl:11])[C:8]([S:12](=[O:15])(=[O:14])[NH2:13])=[CH:7][C:5]=1[NH2:6].[C:16]12(C(O)=O)[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2.[CH4:29]>CO>[OH2:14].[CH:16]12[CH2:17][CH:18]3[CH2:19][CH:20]([CH2:21][CH:22]([CH2:24]3)[CH:23]1[C:29]1[NH:6][C:5]3[CH:7]=[C:8]([S:12](=[O:14])(=[O:15])[NH2:13])[C:9]([Cl:11])=[CH:10][C:4]=3[N:3]=1)[CH2:25]2.[CH:16]12[CH2:17][CH:18]3[CH2:19][CH:20]([CH2:21][CH:22]([CH2:24]3)[CH:23]1[C:29]1[NH:6][C:5]3[CH:7]=[C:8]([S:12](=[O:14])(=[O:15])[NH2:13])[C:9]([Cl:11])=[CH:10][C:4]=3[N:3]=1)[CH2:25]2

Participants

5

Reactant 3

HCID 297MethaneHCID 132351-Adamantanecarboxylic acidHCID 20477848HCID 20477848, compound

Product 1

HCID 70523752HCID 70523752, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 2.95 g of 2-amino-4-chloro-5-sulfamylaniline dihydrochloride and 2.70 g of 1-adamantanecarboxylic acid was ground together and heated at 190°-200° for 5 hours. The dark solid was dissolved in 500 ml of methanol, the methanol brought to a boil, charcoal added, boiling continued for five minutes, and the suspension then filtered through two sheets of filter paper, and then through Celite. Concentration in vacuo provided a solid which was then added to 100 ml of concentrated ammonium hydrozide and stirred for twenty minutes. The crude product was collected by filtration and recrystallized from acetonitrile to provide 0.5 g of colorless crystals, m.p. 207°-210°.

Workup

  1. temperatureheated at 190°-200° for 5 hours
  2. additionadded
  3. filtrationthe suspension then filtered through two sheets of filter paper
  4. concentrationConcentration in vacuo
  5. customprovided a solid which
  6. filtrationThe crude product was collected by filtration
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-e38e4850413848bebccf3521ef066ab7
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

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