Acetonitrile → HCID 21483041, compound

HRID 1415655Notes

Reaction equation

HRID 1415655 reaction equation
[S-:1][C:2]#[N:3].[K+].Cl[C:6]([O:8][CH3:9])=[O:7].C(#N)C.[CH2:13]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=1)[CH2:14][CH2:15][CH3:16]>O>[CH3:9][O:8][C:6]([NH:3][C:2]([NH:21][C:20]1[CH:22]=[CH:23][C:17]([CH2:13][CH2:14][CH2:15][CH3:16])=[CH:18][C:19]=1[N+:24]([O-:26])=[O:25])=[S:1])=[O:7]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6586Methyl chloroformateHCID 77229Benzenamine, 4-butyl-2-nitro-HCID 516872Potassium thiocyanate

Product 1

HCID 21483041HCID 21483041, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

Dry potassium thiocyanate (42.8 g; 0.44 mole), methyl chloroformate (37.8 g; 0.40 mole) and dry acetonitrile (130 ml) were mixed with stirring at laboratory temperature and stirring was continued for 1 hour at 35°-45° C. The mixture was then cooled in an ice bath to 15° C. and 4-n-butyl-2-nitroaniline (38.8 g; 0.2 mole) 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 ethanol to give 1-methoxycarbonyl-3-(4-n-butyl-2-nitrophenyl)thiourea (47.8 g), m.p. 164°-165° C. (with decomposition).

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 ethanol

Sources & evidence

ORD record
ord-d124dcdd66ff43d898394dcee0fefcb5
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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