Dichloromethane → HCID 86634883, compound

HRID 1012987Notes

Reaction equation

HRID 1012987 reaction equation
O=[C:2]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4][NH:3]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:17].ClCCl.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[S:17]=[C:2]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4][NH:3]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 14817Phosphorus sulfide (P2S5)HCID 226177365-Oxo-(1,4)diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 86634883HCID 86634883, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

tert-Butyl 5-oxo-1,4-diazepane-1-carboxylate, P4S10 (0.2 eq.), HMDO (2 eq.) and dichloromethane were combined and stirred magnetically at room temperature for 1 hour. The reaction mixture was then cooled to 0° C. and aqueous K2CO3 solution (1.26 mL of 5.3 M/mmol P4S10 taken) was added. A volume of acetone equal to one half of the reaction solvent was added to obtain a stirrable mixture, and the reaction mixture was stirred vigorously for 30 minutes at 0° C. Volatiles were evaporated, water and ethyl acetate were added, layers were separated and the organic phase was washed with water and brine. The organic extract was dried over Na2SO4 and evaporated, to afford the title compound. 1H NMR (300 MHz, CDCl3) δ 8.7 (bs, 1H), 3.68-3.60 (m, 4H), 3.42-3.38 (m, 2H), 3.15-3.09 (m, 2H), 1.43 (s, 9H); MS (ES) C10H18N2O2S requires 230. Found: 231 (M+H+).

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. customto obtain a stirrable mixture
  3. stirringthe reaction mixture was stirred vigorously for 30 minutes at 0° C
  4. customVolatiles were evaporated
  5. additionwater and ethyl acetate were added
  6. customlayers were separated
  7. washthe organic phase was washed with water and brine
  8. extractionThe organic extract
  9. dry with materialwas dried over Na2SO4
  10. customevaporated

Sources & evidence

ORD record
ord-cebce1f8c6694a259ffdf9ef047a8cdd
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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