Chloroacetaldehyde → 2-(Thiazol-2-ylamino)-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one

HRID 895986Notes

Reaction equation

HRID 895986 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4]2[CH:13]=[CH:14][C:15]([NH:17][C:18]([NH2:20])=[S:19])=[CH:16][C:3]1=2.Cl[CH2:22][CH:23]=O>C(O)C>[S:19]1[CH:23]=[CH:22][N:20]=[C:18]1[NH:17][C:15]1[CH:14]=[CH:13][C:4]2[NH:5][C:6]3[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=3[NH:8][C:2](=[O:1])[C:3]=2[CH:16]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 11300593(11-Oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea

Product 1

HCID 112552822-(Thiazol-2-ylamino)-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-oneYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea (Example 9, 75 mg, 0.26 mmol) in ethanol (10 mL) was added chloroacetaldehyde (50% in water, 0.1 mL). The solution was refluxed for 5 hr and then concentrated under vacuum and poured into water (5 mL). The solution pH was adjusted to 9 with aqueous saturated sodium bicarbonate and then extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent evaporated. The residue was recrystallized from ethanol/hexanes to give yellow solid (30 mg, 40%).

Workup

  1. temperatureThe solution was refluxed for 5 hr
  2. concentrationconcentrated under vacuum
  3. additionpoured into water (5 mL)
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customthe solvent evaporated
  7. customThe residue was recrystallized from ethanol/hexanes

Sources & evidence

ORD record
ord-d1477a17f17a461795fa85913e690b23
Source dataset
uspto-grants-2005_07
Patent number
US06919328B1

Reaction notes

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