Triphosgene → 4-Methoxycarbonylphenyl-pentyl-carbamoyl chloride

HRID 1759780Notes

Reaction equation

HRID 1759780 reaction equation
[CH2:1]([NH:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[Cl:17][C:18](Cl)([O:20]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[CH3:14][O:13][C:11]([C:10]1[CH:9]=[CH:8][C:7]([N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:18]([Cl:17])=[O:20])=[CH:16][CH:15]=1)=[O:12]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 22600039Methyl 4-pentylaminobenzoate

Product 1

HCID 226000294-Methoxycarbonylphenyl-pentyl-carbamoyl chlorideYield 275.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-pentylaminobenzoate (43) (200 mg, 0.91 mmole) in 5 mL of THF was treated with 95 mg of triphosgene (0.35 eq.), stirred at reflux for three hours, then poured onto 50 mL ice-water and extracted with three portions of 50 mL of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give 250 mg of 4-methoxycarbonylphenyl-pentyl-carbamoyl chloride (45) which was used without purification.

Workup

  1. temperatureat reflux for three hours
  2. extractionextracted with three portions of 50 mL of ethyl acetate
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e05fe2475d4436c8b0fc6578183d1b8
Source dataset
uspto-grants-2005_01
Patent number
US06838472B2

Reaction notes

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