Acetonitrile → HCID 21482983, compound

HRID 1415656Notes

Reaction equation

HRID 1415656 reaction equation
[S-:1][C:2]#[N:3].[K+].Cl[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(#N)C.[CH2:14]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[C:20]([N+:25]([O-:27])=[O:26])[CH:19]=1)[CH2:15][CH2:16][CH3:17]>O>[CH2:9]([O:8][C:6]([NH:3][C:2]([NH:22][C:21]1[CH:23]=[CH:24][C:18]([CH2:14][CH2:15][CH2:16][CH3:17])=[CH:19][C:20]=1[N+:25]([O-:27])=[O:26])=[S:1])=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10928Ethyl chloroformateHCID 77229Benzenamine, 4-butyl-2-nitro-HCID 516872Potassium thiocyanate

Product 1

HCID 21482983HCID 21482983, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

Dry potassium thiocyanate (18.5 g), ethyl chloroformate (15.6 g) and dry acetonitrile (65 ml) were mixed with stirring at laboratory temperature and stirring was continued for 1 hour at 45°-55° C. The mixture was then cooled in an ice bath to 15° C. and 4-n-butyl-2-nitroaniline (19.0 g) was added in portions with stirring during 15 minutes, the temperature of the stirred reaction mixture being maintained between 15 and 18° C. during the addition. When the addition was complete the mixture was stirred at 15° C. for 2 hours, poured into water (1 litre), and the yellow solid which separated was filtered off and washed with water. This crude product was recrystallised from cyclohexane to give 1-ethoxycarbonyl-3-(4-n-butyl-2-nitrophenyl)thiourea (26.9 g), m.p. 121°-123° C.

Workup

  1. stirringstirring
  2. stirringwith stirring during 15 minutes
  3. customthe temperature of the stirred reaction mixture
  4. temperaturebeing maintained between 15 and 18° C. during the addition
  5. additionWhen the addition
  6. stirringwas stirred at 15° C. for 2 hours
  7. customthe yellow solid which separated
  8. filtrationwas filtered off
  9. washwashed with water
  10. customThis crude product was recrystallised from cyclohexane

Sources & evidence

ORD record
ord-74e24715a25647f5b0bcca4000331ea4
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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