Water → 4-(2-Chloro-ethyl)-1-[(E)-3-(3-chloro-phenyl)-acryloyl]-[1,4]diazepan-5-one

HRID 1867405Notes

Reaction equation

HRID 1867405 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH2:21]O)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.CS([Cl:34])(=O)=O.O>ClCCl>[Cl:34][CH2:21][CH2:20][N:15]1[C:16](=[O:19])[CH2:17][CH2:18][N:12]([C:10](=[O:11])/[CH:9]=[CH:8]/[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 684339731-[(E)-3-(3-chloro-phenyl)-acryloyl]-4-(2-hydroxy-ethyl)-[1,4]diazepan-5-one

Product 1

HCID 684323164-(2-Chloro-ethyl)-1-[(E)-3-(3-chloro-phenyl)-acryloyl]-[1,4]diazepan-5-oneYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 2.13 g (3.50 mmol) of 1-[(E)-3-(3-chloro-phenyl)-acryloyl]-4-(2-hydroxy-ethyl)-[1,4]diazepan-5-one and 0.73 ml (5.25 mmol) of Et3N in 35 ml of dichloromethane were added 0.29 ml (3.68 mmol) of methanesulfonyl chloride under stirring within 5 min keeping the temperatue at 0° C. The reaction was stirred at room temperature for 1 h 45 min. Water was added and after 5 min, the reaction was then partitioned between ether and aqueous saturated NaHCO3. The water phase was extracted again with ether (2×), the organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and concentrated to yield 1.22 g (87%) of the title compound as yellow viscous oil. MS: 341.0 (MH+, 2Cl).

Workup

  1. customat 0° C
  2. stirringThe reaction was stirred at room temperature for 1 h 45 min
  3. customthe reaction was then partitioned between ether and aqueous saturated NaHCO3
  4. extractionThe water phase was extracted again with ether (2×)
  5. washthe organic phases were washed with aqueous 10% NaCl
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-db1dcf3cc5174630aebc3443d9cf6b5c
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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