Hydrochloric Acid → HCID 86737509, compound

HRID 1414014Notes

Reaction equation

HRID 1414014 reaction equation
[N:1](=[C:3]1[CH2:12][C:8]2[S:9][CH:10]=[CH:11][C:7]=2[C:6](=[CH2:13])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)[OH:2].C([BH3-])#N.[Na+].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.Cl>CO>[NH:1]([CH:3]1[CH2:12][C:8]2[S:9][CH:10]=[CH:11][C:7]=2[C:6](=[CH2:13])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)[OH:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5003444Sodium cyanoborohydrideHCID 86737510HCID 86737510, compound

Product 1

HCID 86737509HCID 86737509, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

9-Hydroximino-4-methylene-9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophene (5.7 g), sodium cyanoborohydride (5.4 g) and methyl orange (0.05 g) are stirred in methanol (150 ml). A solution of concentrated HCl in methanol (1:1 v/v) is added dropwise at a rate sufficient to maintain the mixture at the indicator turning point until thin layer chromatography (silica gel plate, methylene chloride elution) indicates the starting oxime has been consumed (2-3 hours). The mixture is evaporated to dryness in vacuo and the residue is treated with water (250 ml) and adjusted to pH 8 with concentrated ammonia. The mixture is extracted with ether (3×80 ml) and the combined ether layers are washed with water, dried over sodium sulfate, filtered and evaporated to dryness in vacuo to give 9-hydroxamino-4-methylene-9,10-dihydro-4H-benzo[4,5]cyclohepta-[1,2-b]thiophene.

Workup

  1. temperatureto maintain the mixture at the indicator
  2. washuntil thin layer chromatography (silica gel plate, methylene chloride elution)
  3. customhas been consumed (2-3 hours)
  4. customThe mixture is evaporated to dryness in vacuo
  5. additionthe residue is treated with water (250 ml)
  6. extractionThe mixture is extracted with ether (3×80 ml)
  7. washthe combined ether layers are washed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-8410d3769e444d238ad4259f8e2be98c
Source dataset
uspto-grants-1981_02
Patent number
US04252810

Reaction notes

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