Ammonia → Thiourea, (3-chlorophenyl)- (9CI)

HRID 1506803Notes

Reaction equation

HRID 1506803 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]=[C:9]=[S:10])[CH:3]=1.[NH3:11]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH2:11])=[S:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 754493-Chlorophenyl isothiocyanate

Product 1

HCID 2734794Thiourea, (3-chlorophenyl)- (9CI)Yield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Chloro-3-isothiocyanatobenzene (15 g, 88 mmol) was added to a solution of 0.5 M ammonia in 1,4-dioxane (80 mL), and the mixture was stirred at room temperature for 0.16 h. The reaction mixture was concentrated in vacuo, and partitioned between ethyl acetate and water. The separated organic layer was washed with saturated NaCl solution, dried over sodium sulfate and filtered, and the filtrate was concentrated in vacuo to afford the title compound (15.5 g, 89%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 9.80 (s, 1H), 7.70 (s, 1H), 7.52 (bs, 2H), 7.38-7.27 (m, 2H), 7.15 (dt, J1=7.0 Hz, J2=2.1 Hz, 1H). ESI-MS m/z: 187 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between ethyl acetate and water
  3. washThe separated organic layer was washed with saturated NaCl solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3015bcaec7a44396a9ce6bc445c051ac
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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