Phosgene → HCID 5279166, compound

HRID 729339Notes

Reaction equation

HRID 729339 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.C(Cl)(Cl)=O.ClC1C=C(C=CC=1Cl)[C:25]([NH:27][CH:28]1[C:34](=[O:35])[NH:33][C:32]2[CH:36]=[CH:37][CH:38]=[CH:39][C:31]=2[C:30]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[N:29]1)=[O:26]>ClCCl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][C:25]([NH:27][CH:28]1[C:34](=[O:35])[NH:33][C:32]2[CH:36]=[CH:37][CH:38]=[CH:39][C:31]=2[C:30]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[N:29]1)=[O:26]

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 70002-MethoxyanilineHCID 8471TriethylamineHCID 5279119HCID 5279119, compound

Product 1

HCID 5279166HCID 5279166, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methoxy-aniline (37 mg) in dry dichloromethane (3 ml) was treated with triethylamine (0.04 ml) followed by 20% phosgene in toluene (0.08 ml). The mixture was stirred at room temperature for 1 h, and then Intermediate 3 (37 mg) was then added, and the stirring continued for 18 h. The mixture was partitioned between water and ethyl acetate. The organic layer was passed through a hydrophobic frit and evaporated and the residue was purified on a silica gel SPE cartridge. Gradient elution with 0-5% methanol in dichloromethane gave the title compound as a colourless solid (24 mg).

Workup

  1. waitthe stirring continued for 18 h
  2. customThe mixture was partitioned between water and ethyl acetate
  3. customevaporated
  4. customthe residue was purified on a silica gel SPE cartridge
  5. washGradient elution with 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-07f0e536cb1b4e39b954fd77df0a7e7c
Source dataset
uspto-grants-2009_09
Patent number
US07582624B2

Reaction notes

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