Formic Acid → HCID 19785214, compound

HRID 256533Notes

Reaction equation

HRID 256533 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:16][NH:17][CH2:18][CH2:19][C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:26](O)=O.C=O>CN(C)C=O>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:16][N:17]([CH3:26])[CH2:18][CH2:19][C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 19785212HCID 19785212, compound

Product 1

HCID 19785214HCID 19785214, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-phenylsulphonyl-1,4,5,6,7,8-hexahydro-8-phenylpyrrolo[2,3-d]azepine (1.24 g), formic acid (0.86 gm), 40% formaldehyde (1.3 ml), and dimethylformamide (30 ml) were refluxed for 1 hour. After evaporating to dryness, 5M hydrochloric acid was added to the residue and the solution was washed with ether three times. The aqueous solution was basified with 5M sodium hydroxide and the product was extracted into dichloromethane. The extracts were washed with water, dried and evaporated to give a solid, m.p. 115°-116° C. (ethanol).

Workup

  1. temperaturewere refluxed for 1 hour
  2. customAfter evaporating to dryness, 5M hydrochloric acid
  3. additionwas added to the residue
  4. washthe solution was washed with ether three times
  5. extractionthe product was extracted into dichloromethane
  6. washThe extracts were washed with water
  7. customdried
  8. customevaporated
  9. customto give a solid, m.p. 115°-116° C. (ethanol)

Sources & evidence

ORD record
ord-6f7e0fe3fc1042c298e3802c4db728f8
Source dataset
uspto-grants-1993_11
Patent number
US05258378

Reaction notes

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