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Dichloromethane → 5-Chloro-3-(4-nitrophenyl)-1,2,4-thiadiazole

HRID 464704
Notes
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Reaction equation

HRID 464704 reaction equation
[OH-].[Na+].Cl.[N+:4]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=[NH:12])=[CH:9][CH:8]=1)([O-:6])=[O:5].[Cl:16][C:17]([SH:20])(Cl)Cl.ClCCl>O>[Cl:16][C:17]1[S:20][N:13]=[C:11]([C:10]2[CH:9]=[CH:8][C:7]([N+:4]([O-:6])=[O:5])=[CH:15][CH:14]=2)[N:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 1706254-Nitrobenzamidine hydrochloride

Product 1

HCID 202163765-Chloro-3-(4-nitrophenyl)-1,2,4-thiadiazoleYield 40.3%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A solution of 75.6 gm of sodium hydroxide in 100 ml of water was added to a stirred mixture of 101.4 gm of p-nitrobenzamidine hydrochloride, 70 gm of perchloromethyl mercaptan and 760 ml of dichloromethane, while keeping the temperature below -5° C. After additional 2 hours at -5° C., the resulting suspension was filtered, and the organic phase was separated, evaporated to dryness, and the residual solid was recrystallized from 95% ethanol, yielding 45 gm of the title compound, m.p. 143°-145° C.

Workup

  1. customthe temperature below -5° C
  2. filtrationthe resulting suspension was filtered
  3. customthe organic phase was separated
  4. customevaporated to dryness
  5. customthe residual solid was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-b56a310b0915491a95f79994ff1d025a
Source dataset
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04548944

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes