Ethanol → HCID 66869265, compound

HRID 627863Notes

Reaction equation

HRID 627863 reaction equation
[N:1]1[C:11]2[C:10]3[S:12][C:13]([C:15]4[N:16]=[C:17]([NH:27]C(C)=O)[N:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=5[Cl:26])[CH:19]=4)=[CH:14][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(O)C.S(=O)(=O)(O)O>C([O-])([O-])=O.[Na+].[Na+]>[N:1]1[C:11]2[C:10]3[S:12][C:13]([C:15]4[N:16]=[C:17]([NH2:27])[N:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=5[Cl:26])[CH:19]=4)=[CH:14][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 66868646HCID 66868646, compound

Product 1

HCID 66869265HCID 66869265, compound

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

From Example 37, 4-(6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)-(2-chlorophenyl)-2-amino-1H-imidazole 127 (27 mg, 0.062 mmol) was added to ethanol (2 mL, 30 mmol) containing 1 ml of 10% aqueous sulfuric acid. The reaction was microwaved on 300 watts at 100° C. for 15 minutes. The reaction mixture was mixed with 10 ml of 1 M aq Na2CO3 and extracted with ethyl acetate twice. The organic layer was washed with brine and dried over K2CO3. The solvent was evaporated to afford 128. (18 mg, 74%). MS (ESI+) 395.1

Workup

  1. customThe reaction was microwaved on 300 watts at 100° C. for 15 minutes
  2. extractionextracted with ethyl acetate twice
  3. washThe organic layer was washed with brine
  4. dry with materialdried over K2CO3
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-703404482240453492671e8a123c704d
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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