Phosgene → HCID 22600036, compound

HRID 1759777Notes

Reaction equation

HRID 1759777 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH3:18])([CH3:17])[CH2:12][CH2:11][C:10]([CH3:20])([CH3:19])[C:9]=2[CH:8]=1)[CH3:2].[C:21](Cl)(Cl)=[O:22].[NH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][CH2:4][CH2:5][N:6]([C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH3:18])([CH3:17])[CH2:12][CH2:11][C:10]([CH3:19])([CH3:20])[C:9]=2[CH:8]=1)[C:21](=[O:22])[NH:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:34][CH:35]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 12082Methyl 4-aminobenzoateHCID 22600030HCID 22600030, compound

Product 1

HCID 22600036HCID 22600036, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of (2-ethoxy-ethyl)-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (37) (484 mg, 1.76 mmole) in 5 mL toluene was treated with 0.96 mL of a 20% phosgene solution in toluene, stirred at room temperature for 12 hours and then concentrated in vacuo. The residue was diluted with 7.2 mL of pyridine and treated with 530 mg of methyl p-aminobenzoate (2 eq.), heated at 40° C. for 15 hours, then concentrated in vacuo to give an orange oil. The product was purified by flash chromatography (SiO2, 15% ethyl acetate/hexanes, dry pack) to provide 520 mg (44%) of methyl 4-[3-(2-ethoxy-ethyl)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (39) as a colorless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with 7.2 mL of pyridine
  3. temperatureheated at 40° C. for 15 hours
  4. concentrationconcentrated in vacuo
  5. customto give an orange oil
  6. customThe product was purified by flash chromatography (SiO2, 15% ethyl acetate/hexanes, dry pack)

Sources & evidence

ORD record
ord-bf2e1953b24f4b629d1c11e68faa18ad
Source dataset
uspto-grants-2005_01
Patent number
US06838472B2

Reaction notes

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