Diethyl Ether → HCID 13071635, compound

HRID 2198555Notes

Reaction equation

HRID 2198555 reaction equation
[S:1]1[C:5]([SH:6])=[N:4][N:3]=[C:2]1[SH:7].[CH3:8][N:9]=[C:10]=[O:11].[CH2:12]([N:14]([CH2:17]C)CC)C.CC[O:21]CC>>[CH3:8][NH:9][C:10]([S:7][C:2]1[S:1][C:5]([S:6][C:12](=[O:21])[NH:14][CH3:17])=[N:4][N:3]=1)=[O:11]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 178418558HCID 178418558, compound

Product 1

HCID 13071635HCID 13071635, compound

Conditions

Temperature
25 °C

Procedure

A solution of 7.5 g (0.05 mole) of 1,3,4- thiadiazole-2,5-dithiol (DMTD) was stirred in 700 ml of anhydrous ether in a 3-necked round-bottom flask equipped with a thermometer, a reflux condenser, a dropping funnel, and a magnetic stirrer. The solution was maintained at below 25° C. by cooling while 5.9 ml (0.1 mole) of methyl isocyanate and 0.2 ml of triethylamine were added dropwise. The reaction mixture was stirred at 25° C. for 48 hours. The yellow-solid crystals were collected on a filter, washed with ether and dried. The product was 8.2 grams (62 mole % yield) m.p. 162° C., 2,5-bis(N-methylcarbamylthio)-1,3,4-thiadiazole.

Workup

  1. customequipped with a thermometer, a reflux condenser, a dropping funnel, and a magnetic stirrer
  2. temperatureThe solution was maintained at below 25° C.
  3. additionwere added dropwise
  4. customThe yellow-solid crystals were collected on a filter
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-239e219573cc424eba6038ac711b3d22
Source dataset
uspto-grants-1982_11
Patent number
US04358597

Reaction notes

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