Chloroacetyl chloride → HCID 57624569, compound

HRID 1172868Notes

Reaction equation

HRID 1172868 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([NH2:14])=[CH:13][C:7]=2[CH:6]=1)=[O:4].CN1CCOCC1.[Cl:22][CH2:23][C:24](Cl)=[O:25]>C(Cl)Cl.C1COCC1.CCOC(C)=O.O>[Cl:22][CH2:23][C:24]([NH:14][C:12]1[CH:11]=[CH:10][C:8]2[S:9][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][C:7]=2[CH:13]=1)=[O:25]

Participants

7

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 79724-MethylmorpholineHCID 2824064Methyl 5-amino-1-benzothiophene-2-carboxylate

Product 1

HCID 57624569HCID 57624569, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a solution of 5-amino-benzo[b]thiophene-2-carboxylic acid methyl ester (989 mg, 4.79 mmol) in CH2Cl2/THF (5/5 mL) was added NMM (630 μL, 5.73 mmol) and chloroacetylchloride (415 μL, 5.25 mmol). After stirring 2.5 h, the mixture was diluted with EtOAc and H2O, and the solid was filtered yielding a pale-white solid, which was used without further purification. MS: cal'd (MH+) 284, exp (MH+) 284.

Workup

  1. filtrationthe solid was filtered
  2. customyielding a pale-white solid, which
  3. customwas used without further purification

Sources & evidence

ORD record
ord-670e5bac1978409b8727b163260c22d0
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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