Phosgene → HCID 86623920, compound

HRID 1666500Notes

Reaction equation

[C:1]([Cl:4])(Cl)=[O:2].Cl.[NH:6]1[CH2:11][CH2:10][C:9](=[CH:12][C:13]2[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=2)[CH2:8][CH2:7]1>C1(C)C=CC=CC=1.C(N(C(C)C)CC)(C)C.ClCCl>[F:26][C:23]([F:24])([F:25])[C:20]1[CH:21]=[CH:22][C:17]([O:16][C:15]2[CH:14]=[C:13]([CH:29]=[CH:28][CH:27]=2)[CH:12]=[C:9]2[CH2:8][CH2:7][N:6]([C:1]([Cl:4])=[O:2])[CH2:11][CH2:10]2)=[N:18][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 100 mL round-bottomed flask was fitted with a stirring bar and dropping funnel. To the reaction flask was added dichloromethane (30 mL) and the vessel was set to chill in an ice/water bath. To the flask was added 19% v/v phosgene in toluene (6 mL). 2-(3-piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (3.34 g, 9 mmol, from Example 1a, Step 5) was dissolved in a 15% v/v solution of diisopropylethylamine in dichloromethane and added to the chilled reaction flask slowly using the dropping funnel. Upon addition, the solution was stirred at 0° C. for 1 h. Upon completion of the reaction, the solvent and excess phosgene were removed in vacuo. A 0.2 M stock solution of the residue in dichloroethane was prepared for use in the next step (45 mL).

Workup

customA 100 mL round-bottomed flask was fitted with a stirring bar
temperatureto chill in an ice/water bath
additionadded to the chilled reaction flask
additionUpon addition
customUpon completion of the reaction
customthe solvent and excess phosgene were removed in vacuo
customA 0.2 M stock solution of the residue in dichloroethane was prepared for use in the next step (45 mL)

Sources & evidence

ORD record: ord-e131cfc3ff81418495ea9911d47d139d
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044052B2

Reaction notes

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