Hydrochloric Acid → HCID 58679133, compound

HRID 18943Notes

Reaction equation

HRID 18943 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:11].Cl.[O:13]1CCOC[CH2:14]1.C(Cl)(Cl)=O>C1COCC1>[Cl:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[N:11]=[C:14]=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 312751,4-DioxaneHCID 58679182HCID 58679182, compound

Product 1

HCID 58679133HCID 58679133, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a vial containing 4-chlorobenzo[d][1,3]dioxol-5-amine (28.8 mg, 0.168 mmol, 1 equiv.) in 1 mL THF was added 4M HCl in 1,4-dioxane (0.042 mL, 1 equiv.) followed by phosgene (20% in toluene; 0.360 mL, 0.684 mmol, 4 equiv.). The vial was capped and heated to 70° C. for 1 h, the solvent was removed under, the residue redissolved in toluene and solvent was again removed under vacuum to eliminate any remaining phosgene yielding 4-chloro-5-isocyanatobenzo[d][1,3]dioxole used as such in the next step.

Workup

  1. customThe vial was capped
  2. customthe solvent was removed under, the residue
  3. dissolutionredissolved in toluene
  4. customsolvent was again removed under vacuum

Sources & evidence

ORD record
ord-dd6ff86954744922a24da377a7d58ba8
Source dataset
uspto-grants-2010_06
Patent number
US07741479B2

Reaction notes

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