Toluene → HCID 90039554, compound

HRID 530268Notes

Reaction equation

HRID 530268 reaction equation
C[N:2]([CH3:6])[C:3]([NH2:5])=[S:4].C1(C)C=CC=CC=1.[C:14](=O)([O-])[O-].[Na+].[Na+].Cl[C:21]([O:23][CH3:24])=[O:22]>O>[CH3:6][N:2]([C:3](=[S:4])[NH:5][CH3:14])[C:21](=[O:22])[O:23][CH3:24]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 30341921,1-Dimethyl-2-thiourea

Product 1

HCID 90039554HCID 90039554, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

420.9 g (4.00 mol) N,N-dimethylthiourea with a purity of 99% were charged to 2000 g toluene. 507 g (4.78 mol) sodium carbonate was added and the suspension heated to 65° C. Afterwards 432.2 g (4.60 mol) methyl chloroformate were dosed in over 5 h at 65° C. The mixture was poststirred at the same temperature over 0.5 h. For work up, demineralized water was added under agitation and the phases separated. The aqueous phase was extracted with 800 g toluene and the organic phases were combined. The product content of the organic solution was determined with 15.15% by quant. HPLC (HPLC-method A; tR=3.6 min), which corresponds to a chemical yield of 90.3%.

Workup

  1. customwere dosed in over 5 h at 65° C
  2. additionwas added under agitation
  3. customthe phases separated
  4. extractionThe aqueous phase was extracted with 800 g toluene

Sources & evidence

ORD record
ord-b14eaa2c54df4a34b17b7819aea7f0e5
Source dataset
uspto-grants-2016_05
Patent number
US09353070B2

Reaction notes

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