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Trichloromethanethiol → 5-Chloro-3-cyclohexyl-1,2,4-thiadiazole

HRID 714403
Notes
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Reaction equation

HRID 714403 reaction equation
[CH:1]1([C:7](=[NH:9])[NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[Cl:19][C:20]([SH:23])(Cl)Cl>C(Cl)Cl>[Cl:19][C:20]1[S:23][N:8]=[C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6390TrichloromethanethiolHCID 81531DiisopropylethylamineHCID 193051Cyclohexylcarboxamidine

Product 1

HCID 652672555-Chloro-3-cyclohexyl-1,2,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

Cyclohexanecarboximidamide (100 mg, 792 μmol) and DIPEA (512 mg, 3.96 mmol) in 10 mL DCM at 0-5° C. were treated with perchloromethyl mercaptan (147 mg, 792 μmol) in 5 mL DCM and stirred for 1 hr at 0-5° C. The mixture was concentrated in vacuo to give a brown solid which was used with out further purification in the subsequent step.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a brown solid which
  3. customwas used with out further purification in the subsequent step

Sources & evidence

ORD record
ord-10a225bb09934310b118e4aec0f41614
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187440B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes