Trichloromethanethiol → 5-Chloro-3-p-tolyl-[1,2,4]thiadiazole

HRID 651001Notes

Reaction equation

HRID 651001 reaction equation
Cl.[CH3:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:19][C:20]([SH:23])(Cl)Cl>C(Cl)(Cl)Cl>[C:3]1([CH3:2])[CH:11]=[CH:10][C:6]([C:7]2[N:9]=[C:20]([Cl:19])[S:23][N:8]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6390TrichloromethanethiolHCID 8471TriethylamineHCID 1227534-Methylbenzene-1-carboximidamide hydrochloride

Product 1

HCID 226110665-Chloro-3-p-tolyl-[1,2,4]thiadiazoleYield 44%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
5 °C

Procedure

To a mixture of p-methylbenzamidine hydrochloride (5.1 g, 30.0 mmol) in CHCl3 (100 ml) is added triethyl amine (15.12 g, 20.9 ml, 150.0 mmol) and cooled to 5° C. in an ice-water bath. To the mixture is slowly added perchloromethyl mercaptan (95%, 6.16 g, 31.5 mmol) in CHCl3(10 ml) over 1 hour. The yellow solution is allowed to warm up to room temperature. After 2 hours the mixture is washed with water (100 ml×2) and brine (100 ml). The organic layer is dried over MgSO4 and the solvent is removed under reduced pressure to yield a brown oil. The oil is purified on a bed of silica gel, eluting with 1:1 CHCl3:hexanes to yield 3-(p-tolyl)-5-chloro-1,2,4-thiadiazole as a yellow solid (2.78 g, 44%).

Workup

  1. customover 1 hour
  2. temperatureto warm up to room temperature
  3. washAfter 2 hours the mixture is washed with water (100 ml×2) and brine (100 ml)
  4. dry with materialThe organic layer is dried over MgSO4
  5. customthe solvent is removed under reduced pressure
  6. customto yield a brown oil
  7. customThe oil is purified on a bed of silica gel
  8. washeluting with 1:1 CHCl3

Sources & evidence

ORD record
ord-018d9ffa290f4ff39b809de54293a8b3
Source dataset
uspto-grants-2001_08
Patent number
US06277873B1

Reaction notes

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