1,2-Dichloroethane → (2-Chloro-5-phenyl-thiophen-3-yl)-[1,4]oxazepan-4-yl-methanone

HRID 2068601Notes

Reaction equation

HRID 2068601 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([OH:9])=O.C(Cl)CCl.[O:20]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.O>C(Cl)Cl>[Cl:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([N:23]1[CH2:24][CH2:25][CH2:26][O:20][CH2:21][CH2:22]1)=[O:9]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 218732751,4-OxazepaneHCID 581102042-Chloro-5-phenylthiophene-3-carboxylic acid

Product 1

HCID 44225124(2-Chloro-5-phenyl-thiophen-3-yl)-[1,4]oxazepan-4-yl-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-5-phenyl-thiophene-3-carboxylic acid (1 eq.) in DCM (1 mL/100 mg SM) was added EDC (1.5 eq.). This mixture was stirred at room temperature for 5 minutes and then [1,4]oxazepane (1.2 eq.) was added and the mixture was allowed to stir for 18 hours. Water (1 mL/100 mg SM) was then added and the organic layer separated, dried and evaporated to give the crude product which was purified by column chromatography (EtOAc/iso-hexane). LCMS m/z 322 [M+H]+ R.T.=3.34 mins (Analytical Method 3).

Workup

  1. stirringto stir for 18 hours
  2. customthe organic layer separated
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-ba7ac752a7524d54af8d4e8b8b43a3ac
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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