Oxalyl chloride → Dichloromethane

HRID 2304641Notes

Reaction equation

HRID 2304641 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[CH:4][CH:3]=1.[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([Cl:36])=[O:35])=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:37]([Cl:42])(=O)C(Cl)=O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:34](=[O:35])[CH2:33][C:30]2[CH:31]=[CH:32][C:27]([O:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:28][CH:29]=2)=[CH:6][CH:7]=1.[CH2:37]([Cl:42])[Cl:36]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 113574424-Benzyloxyphenylacetyl ChlorideHCID 23440722(4-Fluoro-phenyl)-[2-(3-methoxy-phenyl)-ethyl]-amine

Product 2

HCID 6344DichloromethaneYield 387.7%HCID 23440755N-(4-Fluorophenyl)-N-{2-(3-methoxyphenyl)ethyl}-2-{4-(phenylmethoxy)phenyl}acetamide

Procedure

The title compound was prepared as described in Example 1.C, using (4-fluorophenyl){2-(3-methoxyphenyl)ethyl}amine (14.2 g, 58 mmol) and 4-benzyloxyphenylacetyl chloride (15.1 g, 58 mmol) prepared from the corresponding carboxylic acid (14.0 g, 58 mmol) and oxalyl chloride (6.5 mL, 75 mmol) in CH2Cl2 (150 mL) (19.1 g, 70% yield): ES-MS (m/z) 470 [M+H]+.

Sources & evidence

ORD record
ord-96c8f80652fa4a0db3cc2c934e38efda
Source dataset
uspto-grants-2002_08
Patent number
US06436923B1

Reaction notes

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