Water → HCID 21483060, compound

HRID 1415624Notes

Reaction equation

HRID 1415624 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][Cl:7])=[O:3].[S-:8][C:9]#[N:10].[K+].[C:12]1([NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18].O>C(#N)C>[Cl:7][CH2:6][CH2:5][O:4][C:2]([NH:10][C:9]([NH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH2:19])=[S:8])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7243O-PhenylenediamineHCID 123052-Chloroethyl chloroformateHCID 516872Potassium thiocyanate

Product 1

HCID 21483060HCID 21483060, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-Chloroethyl chloroformate (14.3 g; 0.10 mole) was added dropwise to a stirred suspension of potassium thiocyanate (11.7 g; 0.12 mole) in dry acetonitrile (100 ml). The temperature of the reaction mixture rose spontaneously to 40° C. and stirring was continued for two hours at 30° C. to 40° C. The reaction mixture was then filtered and the clear filtrate was added dropwise during fifteen minutes to a stirred suspension of o-phenylenediamine (10.8 g; 0.10 mole) in dry acetonitrile (50 ml), the temperature during the addition being maintained between 15°C. and 20° C. by external cooling. When the addition was complete the reaction mixture was stirred at 30° to 40° C. for two hours, and poured into water (1litre). The crude solid which separated was filtered off, washed with water and crystallised from methanol to give 1-(2-chloroethoxycarbonyl)-3-(2-aminophenyl)thiourea (14.9 g), m.p. 173°-174°C. (with decomposition).

Workup

  1. customrose spontaneously to 40° C.
  2. filtrationThe reaction mixture was then filtered
  3. additionthe temperature during the addition
  4. temperaturebeing maintained between 15°C. and 20° C. by external cooling
  5. additionWhen the addition
  6. stirringwas stirred at 30° to 40° C. for two hours
  7. customThe crude solid which separated
  8. filtrationwas filtered off
  9. washwashed with water
  10. customcrystallised from methanol

Sources & evidence

ORD record
ord-6d2cfd853b4940b79a06d4bb9689d5ff
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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