Formaldehyde → HCID 53849774, compound

HRID 342470Notes

Reaction equation

HRID 342470 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].C=O.[C:28]([BH3-])#N.[Na+]>C(O)(=O)C.C(#N)C>[Cl:25][C:3]1[C:2]([NH:1][CH3:28])=[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 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 54054228HCID 54054228, compound

Product 1

HCID 53849774HCID 53849774, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-(3-amino-2,6-dichlorobenzoylamino)-1,2,3,4-tetrahydrodibenzofuran (100 mg), aqueous 37% formaldehyde, sodium cyanoborohydride (70 mg) and acetic acid (5 drops) in acetonitrile (2 ml) was stirred at ambient temperature for 3 hours. The reaction mixture was partitioned between dichloromethane and aqueous saturated sodium bicarbonte. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC on silica gel and the obtained oil was crystallized from diisopropyl ether to give 6-(2,6-dichloro-3-methylaminobenzoylamino)-1,2,3,4-tetrahydrodibenzofuran (21 mg).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and aqueous saturated sodium bicarbonte
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC on silica gel
  7. customthe obtained oil was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-8b885e6810984d0a98ee208c66c13287
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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