Thiophenol → HCID 15593669, compound

HRID 615125Notes

Reaction equation

HRID 615125 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[C:6](Cl)=[N:5][S:4][N:3]=1.C(N(CC)CC)C.[C:17]1([SH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(OCC)C>[Cl:1][C:2]1[C:7](=[O:8])[C:6]([S:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:5][S:4][N:3]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 3540263,5-Dichloro-4H-1,2,6-thiadiazin-4-one

Product 1

HCID 15593669HCID 15593669, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 3.66 g of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one, 30 ml of ethyl ether, and 2.02 g of triethylamine is stirred at 0°-5° C. while a solution of 2.20 g of thiophenol in 20 ml of ethyl ether is added dropwise to it. This mixture is stirred 2 hours longer while it is allowed to return to ambient temperature. Then it is filtered to remove triethylamine hydrochloride, and the filtrate is concentrated on a rotary evaporator. The solid residue is recrystallized from hexane to yield yellow prisms, mp 100°-2°.

Workup

  1. additionis added dropwise to it
  2. customto return to ambient temperature
  3. filtrationThen it is filtered
  4. customto remove triethylamine hydrochloride
  5. concentrationthe filtrate is concentrated on a rotary evaporator
  6. customThe solid residue is recrystallized from hexane
  7. customto yield yellow prisms, mp 100°-2°

Sources & evidence

ORD record
ord-67006511b3bb42c6924cfcbfcf255d65
Source dataset
uspto-grants-1985_02
Patent number
US04497807

Reaction notes

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