Ethanolamine → HCID 178452337, compound

HRID 1253892Notes

Reaction equation

HRID 1253892 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].S=[C:6]1[NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[CH2:9][N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:7]1>C(OC(=O)C)C>[C:20]([O:19][C:17]([N:8]1[CH2:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:6]([NH:1][CH2:2][CH2:3][OH:4])[CH2:7]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 86648334HCID 86648334, compound

Product 1

HCID 178452337HCID 178452337, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-aminoethanol (3.5 mL, 10 mL/mmol) was added to a solution of tert-butyl 2-thioxo-2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate (100 mg, 0.35 mmol), [prepared as described in Example 6, Step 6] and the reaction mixture was heated to reflux for 24 h under nitrogen atmosphere. The reaction mixture was cooled to room temperature, diluted with ethylacetate (50 mL) and washed with water (20 mL). The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to give the desired compound as viscous oil (100.0 mg, 90%) which was used as such for the next step.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 24 h under nitrogen atmosphere
  3. washwashed with water (20 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-84ade5371a1a44be8ca830b412707f64
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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