Acetic Acid → HCID 20319975, compound

HRID 866629Notes

Reaction equation

HRID 866629 reaction equation
O.C(O)(=O)C.[S:6]([N:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][CH2:19][C:18](=[O:27])[CH2:17]1)([C:9]1[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[C-:28]#[N:29].[Na+]>C(O)C>[OH:27][C:18]1([C:28]#[N:29])[CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:16]([S:6]([C:9]2[CH:10]=[CH:11][C:12]([CH3:13])=[CH:14][CH:15]=2)(=[O:7])=[O:8])[CH2:17]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8929Sodium CyanideHCID 679541HCID 679541, compound

Product 1

HCID 20319975HCID 20319975, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

30 ml of water, 40 ml of acetic acid and 20 g of 1,2,4,5-tetrahydro-N-tosyl-[3H]-1-benzazepine-3-one [J. Chem. So., Vol. C (1970), p.2192] were successively added to 300 ml of ethanol and then 20 g of sodium cyanide were added thereto over 2 minutes. The mixture was stirred for 4 hours at room temperature and was then concentrated to 100 ml under reduced pressure. The mixture was extracted with ether and the ether extracts were washed with water, dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness under reduced pressure to obtain 21 g of raw product which was crystallized from a minimum of ether. The mixture was vacuum filtered to obtain 14 g of 3-hydroxy-1-(4-methylphenylsulfonyl)-1,2,4,5-tetrahydro-[3H]-1-benzazepine-3-carbonitrile in the form of colorless crystals melting at 128°C.

Workup

  1. concentrationwas then concentrated to 100 ml under reduced pressure
  2. extractionThe mixture was extracted with ether
  3. washthe ether extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness under reduced pressure
  7. customto obtain 21 g of raw product which
  8. customwas crystallized from a minimum of ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-768c46cac63e4f30a71a5b61aa52665d
Source dataset
uspto-grants-1978_07
Patent number
US04100278

Reaction notes

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