Hydrochloric Acid → HCID 12017713, compound

HRID 2228602Notes

Reaction equation

HRID 2228602 reaction equation
Cl.[NH2:2][CH2:3][C:4]([CH3:7])([SH:6])[CH3:5].Cl.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1.C(N(CC)CC)C.Cl>CN(C=O)C.C(Cl)Cl.CCOCC>[CH3:5][C:4]([SH:6])([CH3:7])[CH2:3][NH:2][C:9]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 130491041-Amino-2-methyl-2-propanethiol hydrochloride

Product 1

HCID 12017713HCID 12017713, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-Amino-2-methylpropane-2-thiol hydrochloride (1.10 g, 6.18 mmol) was dissolved in DMF and nicotinoyl chloride hydrochloride (1.14 g, 8.03 mmol) was slowly added as a solid. The mixture was cooled to 0° C. and triethylamine (3.0 mL, 21.63 mmol) was slowly added. The mixture was stirred for one half hour at 0° C., allowed to warm to room temperature, and stirred overnight. The reaction mixture was diluted with methylene chloride, washed with saturated sodium bicarbonate, brine, and dried over magnesium sulfate. The volatiles were removed under reduced pressure to give a pink oil. An excess of hydrogen chloride in ether was added to precipitate 831 mg. (55%) of the title compound, mp. 163-165° C. 1H NMR (300 MHz, DMSO) δ9.00 (br s, 1H), 8.71 (dd, 1H, J=2.0, 4.9), 8.20 (dt, 1H, J=2.0, 7.9), 7.51 (dd, 1H, J=4.9, 7.9), 3.44 (d, 2H, J=6.3), 1.32 (s, 6H).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. washwashed with saturated sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe volatiles were removed under reduced pressure
  6. customto give a pink oil
  7. customto precipitate 831 mg

Sources & evidence

ORD record
ord-277c1dc540504ecab38f2fd6f1c048b7
Source dataset
uspto-grants-2002_07
Patent number
US06417207B1

Reaction notes

Loading…