Diphosgene → HCID 57853898, compound

HRID 1041813Notes

Reaction equation

HRID 1041813 reaction equation
[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[C:9]([NH2:16])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[O:18]=[C:19](Cl)OC(Cl)(Cl)Cl>C1COCC1.ClCCl>[C:1]([O:5][C:6]([C:7]1[CH:12]=[CH:11][C:10]2[CH2:13][CH2:14][O:15][C:19](=[O:18])[NH:16][C:9]=2[CH:8]=1)=[O:17])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 10426DiphosgeneHCID 578538713-Amino-4-(2-hydroxy-ethyl)-benzoic acid tert-butyl ester

Product 1

HCID 57853898HCID 57853898, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 3-amino-4-(2-hydroxy-ethyl)-benzoic acid tert-butyl ester (2.1 g, 8.86 mmol) in THF (150 mL) and dichloromethane (50 mL) at 0° C. was added diphosgene (0.65 mL, 5.38 mmol) all at once. The reaction turned milky and became clear after 1 minute. The reaction was warmed to room temperature and stirred for 150 minutes. The solvent evaporated to provide 6-oxo-5,6,8,9-tetrahydro-7-oxa-5-aza-benzocycloheptene-3-carboxylic acid tert-butyl ester: MS (m/e) 264 (M+1).

Workup

  1. customThe solvent evaporated

Sources & evidence

ORD record
ord-9480f5b19dca49a0af67e9310e88dece
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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