Ammonia → HCID 15700638, compound

HRID 236797Notes

Reaction equation

HRID 236797 reaction equation
[C:1](O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[CH2:12]([NH:19][C:20]1[C:21]2[CH:34]=[CH:33][CH:32]=[CH:31][C:22]=2[S:23][C:24]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N>O.C1C=CC=CC=1>[CH2:1]([N:19]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:20]1[C:21]2[CH:34]=[CH:33][CH:32]=[CH:31][C:22]=2[S:23][C:24]=1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 243Benzoic AcidHCID 4311764Sodium borohydrideHCID 15700643HCID 15700643, compound

Product 1

HCID 15700638HCID 15700638, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

40.2 g (0.33 mol) of benzoic acid are added to 100 milliliters of absolute benzene and, by cooling and stirring, 3.78 g (0.1 mol) of NaBH4 are added in portions sufficiently slowly for the temperature not to exceed 20° C. After the addition of 6.3 g (20 mmol) of 3-benzylamino-2-phenyl-benzo(b)thiophene the mixture is refluxed for 60 minutes. The still hot reaction mixture has added to it by stirring half a liter of water and is neutralised by ammonia. By evaporating the organic phase dried over K2CO3 and recrystallising the residue in ethanol, 5.1 g (41% of theory) of 3-dibenzylamino-2-phenyl-benzo(b)thiophene are obtained, colourless crystals, mp 98°-100° C.

Workup

  1. temperatureby cooling
  2. customto exceed 20° C
  3. temperatureis refluxed for 60 minutes
  4. additionThe still hot reaction mixture has added to it
  5. customBy evaporating the organic phase
  6. dry with materialdried over K2CO3
  7. customrecrystallising the residue in ethanol

Sources & evidence

ORD record
ord-1006fa3876e342159d0d645667f7e407
Source dataset
uspto-grants-1979_06
Patent number
US04157399

Reaction notes

Loading…