Phenyl isocyanate → HCID 23448222, compound

HRID 1840619Notes

Reaction equation

HRID 1840619 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([NH:11][C:12](=[O:24])[NH:13][C:14]2[CH:21]=[CH:20][C:17]([CH2:18]O)=[CH:16][C:15]=2[O:22][CH3:23])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1(N=C=O)C=CC=CC=1.CCCCCCC>ClCCl>[C:5]1([NH:11][C:12](=[O:24])[NH:13][C:14]2[CH:21]=[CH:20][C:17]([CH2:18][Cl:3])=[CH:16][C:15]=2[O:22][CH3:23])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 8900HeptaneHCID 24386Thionyl ChlorideHCID 69689001HCID 69689001, compound

Product 1

HCID 23448222HCID 23448222, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.55 mL (103.4 mmol) of thionyl chloride were added dropwise to a suspension of 14.07 g (51.7 mmol) of 4-(3-phenylureido)-3-methoxybenzyl alcohol (prepared as described in Example 1, phenyl isocyanate being employed instead of 2-methylphenyl isocyanate) in 200 mL of dichloromethane. The mixture then was stirred at room temperature for 2 hours, allowed to stand overnight and poured onto 800 mL of heptane. The heptane was decanted off from the separated oil, the residue was suspended several times in heptane and in each case the heptane was decanted off. The residue was dissolved in 100 mL of dichloromethane and added dropwise to 800 mL of diisopropyl ether. The mixture was stirred for 1 hour with ice cooling, and the product was filtered off with suction, washed with diisopropyl ether and dried in vacuo.

Workup

  1. customprepared
  2. waitto stand overnight
  3. customThe heptane was decanted off from the separated oil
  4. customin each case the heptane was decanted off
  5. dissolutionThe residue was dissolved in 100 mL of dichloromethane
  6. additionadded dropwise to 800 mL of diisopropyl ether
  7. stirringThe mixture was stirred for 1 hour with ice cooling
  8. filtrationthe product was filtered off with suction
  9. washwashed with diisopropyl ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-640a1a798f314cf08ee44b2075af35b8
Source dataset
uspto-grants-2004_01
Patent number
US06680333B2

Reaction notes

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