Acetic Acid → HCID 21564649, compound

HRID 1579970Notes

Reaction equation

HRID 1579970 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][N:8]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[CH:18]=1.ClC1C=CC2N=CCN=C(C3C=CC=CC=3)C=2C=1.C(O)(=O)C.[SH:41][CH2:42][CH2:43][OH:44]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH:10]([S:41][CH2:42][CH2:43][OH:44])[CH2:9][N:8]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 15672-MercaptoethanolHCID 15539DesmethylmedazepamHCID 278553H-1,4-Benzodiazepine, 7-chloro-5-phenyl-

Product 1

HCID 21564649HCID 21564649, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-chloro-2,3-dihydro-5-phenyl-1H-1,4-benzodiazepine (10 g) was oxidized to 7-chloro-5-phenyl-3H-1,4-benzodiazepine as described in Example 1 with the addition of 0.1 ml of acetic acid. The crude oxidation product was taken up in THF (60 ml), treated with 2-mercaptoethanol (10 ml ) and heated under reflux overnight. The resulting solution was concentrated under reduced pressure until the product began to crystallize and then diluted with 100 ml of ether. The product was collected and washed with ether to give the above-named product as colorless crystals, mp 135°-140° (dec).

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. concentrationThe resulting solution was concentrated under reduced pressure until the product
  4. customto crystallize
  5. additiondiluted with 100 ml of ether
  6. customThe product was collected
  7. washwashed with ether

Sources & evidence

ORD record
ord-f1aaf2d876ba49a9ad4bd27d8f2fb52e
Source dataset
uspto-grants-1976_01
Patent number
US03932399

Reaction notes

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