Chloroacetyl chloride → HCID 70199710, compound

HRID 342468Notes

Reaction equation

HRID 342468 reaction equation
[NH2:1][C:2]1[C:3]([Cl:25])=[C:4]([C:21]([Cl:24])=[CH:22][CH:23]=1)[C:5]([NH:7][C:8]1[C:16]2[O:15][C:14]3[CH2:17][CH2:18][CH2:19][CH2:20][C:13]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:6].[CH2:26]([N:28]([CH2:31]C)[CH2:29]C)[CH3:27].ClCC(Cl)=[O:36].Cl.CNC>C(Cl)(Cl)Cl>[Cl:25][C:3]1[C:2]([NH:1][C:27](=[O:36])[CH2:26][N:28]([CH3:31])[CH3:29])=[CH:23][CH:22]=[C:21]([Cl:24])[C:4]=1[C:5]([NH:7][C:8]1[C:16]2[O:15][C:14]3[CH2:17][CH2:18][CH2:19][CH2:20][C:13]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:6]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 54054228HCID 54054228, compound

Product 1

HCID 70199710HCID 70199710, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 6-(3-amino-2,6-dichlorobenzoylamino)-1,2,3,4-tetrahydrodibenzofuran (100 mg) and triethylamine (54 mg) in chloroform (3 ml) was added chloroacetyl chloride (36 mg) under ice cooling. The mixture was stirred at ambient temperature for 2 hours, and then dimethyl amine hydrochloride (65 mg) was added to the mixture and additionally the mixture was stirred for 12 hours. The mixture was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with (ethyl acetate: n-hexane=1:1) and the obtained oil was crystallized from ethanol to give 6-[2,6-dichloro-3-(2-dimethylaminoacetylamino)benzoylamino]-1,2,3,4-tetrahydrodibenzofuran (62 mg).

Workup

  1. stirringadditionally the mixture was stirred for 12 hours
  2. washThe mixture was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with (ethyl acetate: n-hexane=1:1)
  6. customthe obtained oil was crystallized from ethanol

Sources & evidence

ORD record
ord-e990887753ff40ec8b4c81134dd1d403
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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