Triethylamine → HCID 59715988, compound

HRID 2223783Notes

Reaction equation

HRID 2223783 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][CH:3]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[S:18]([CH3:17])(=[O:20])=[O:19])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 59715989HCID 59715989, compound2×

Product 1

HCID 59715988HCID 59715988, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl [(4-bromophenyl)amino]acetate (intermediate 1, 5.86 g, 20.5 mmol), methanesulfonyl chloride (2.58 g, 1.74 mL, 22.5 mmol), triethylamine (4.15 g, 5.71 mL, 41.0 mmol) and 4-dimethylaminopyridine (260 mg, 2.05 mmol) in dichloromethane (100 mL) was heated at reflux for 14 h. A second portion of methanesulfonyl chloride (2.58 g, 1.74 mmol, 22.5 mmol) was added and heating at reflux continued for a further 48 h. The reaction was cooled to room temperature and extracted with aqueous hydrochloric acid solution (1.0 M; 3×50 mL). The organic phase was dried (magnesium sulfate) and evaporated to dryness. The residue was chromatographed on silica gel (10% diethyl ether:cyclohexane) to give the title compound as a pale cream solid (2.37 g, 32%). LC/MS: 3.35 min; z/e 381 and 383, calcd (M+18) 381 and 383. 1H NMR (400 MHz: CDCl3): 7.55 (2H), 7.35 (2H), 4.30 (2H), 3.10 (3H), 1.45 (9H).

Workup

  1. temperatureat reflux for 14 h
  2. temperatureheating
  3. temperatureat reflux
  4. extractionextracted with aqueous hydrochloric acid solution (1.0 M; 3×50 mL)
  5. dry with materialThe organic phase was dried (magnesium sulfate)
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica gel (10% diethyl ether:cyclohexane)

Sources & evidence

ORD record
ord-ea398a8859a2461b9f58b78bb3f1e4b3
Source dataset
uspto-grants-2008_05
Patent number
US07375248B2

Reaction notes

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