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P-Anisidine → 4-(dimethylamino)-N-(4-methoxyphenyl)benzenecarbothioamide

HRID 4603
Notes
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Reaction equation

HRID 4603 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH3:10][N:11]([CH3:21])[C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=O)=[CH:14][CH:13]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:23]>N1C=CC=CC=1>[CH3:10][N:11]([CH3:21])[C:12]1[CH:20]=[CH:19][C:15]([C:16](=[S:23])[NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:14][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 14817Phosphorus sulfide (P2S5)HCID 44007824-(Dimethylamino)benzoyl chloride

Product 1

HCID 8861264-(dimethylamino)-N-(4-methoxyphenyl)benzenecarbothioamideYield 63.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
30 °C

Procedure

13.6 g of p-anisidine were added to a solution of 22.2 g of 4-dimethylamino-benzoic acid chloride in 84 ml of anhydrous pyridine and the mixture was refluxed for one hour and cooled to 30° C. 33 g of phosphorus pentasulfide were added to the mixture which was refluxed for 2 hours and was then poured into an ice water-concentrated hydrochloric acid mixture. The mixture was stirred for one hour and was vacuum filtered and the product was washed with 0.1N hydrochloric acid. A mixture of the product and 300 ml of N sodium hydroxide solution was stirred for one hour and was vacuum filtered. The product was washed with water and dried to obtain 13.5 g of 4-dimethylamino-N-(4'-methoxyphenyl)-benzenecarbothiamide melting at 192° C.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. temperaturewas refluxed for 2 hours
  3. filtrationfiltered
  4. washthe product was washed with 0.1N hydrochloric acid
  5. additionA mixture of the product and 300 ml of N sodium hydroxide solution
  6. stirringwas stirred for one hour
  7. filtrationfiltered
  8. washThe product was washed with water
  9. customdried

Sources & evidence

ORD record
ord-02572d7994bc44c39cdf4b16503d331d
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04727084

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes