Triethylamine → HCID 21387497, compound

HRID 1833812Notes

Reaction equation

HRID 1833812 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]=[C:10]=[O:11].[OH:12][C:13]1[N:17]=[C:16]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[S:15][N:14]=1>O1CCCC1>[CH3:8][NH:9][C:10]([N:14]1[C:13](=[O:12])[N:17]=[C:16]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[S:15]1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 178519015HCID 178519015, compound

Product 1

HCID 21387497HCID 21387497, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

1 ml of triethylamine and 6.7 g of methyl isocyanate were added to a solution of 14.01 g of 3-hydroxy-5-cyclohexyloxy-1,2,4-thiadiazole in 150 ml of tetrahydrofuran and the mixture was stirred for 2 hours at 20° C, treated with activated carbon, stirred and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was taken up in isopropyl ether. The mixture was vacuum filtered and the recovered crystals were dried to obtain 13.5 g of 2-(N-methylcarbamoyl)-5-cyclohexyloxy-1,2,4-thiadiazole-3-one melting at 121° C.

Workup

  1. additiontreated with activated carbon
  2. stirringstirred
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness under reduced pressure
  5. filtrationfiltered
  6. customthe recovered crystals were dried

Sources & evidence

ORD record
ord-0a16fd76dd1744699478510ebf1637cc
Source dataset
uspto-grants-1978_01
Patent number
US04067720

Reaction notes

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