Hydrochloric Acid → N-[4-Bromo-2-(1-hydroxy-1-thien-2-ylethyl)phenyl]-2-chloroacetamide

HRID 1816872Notes

Reaction equation

HRID 1816872 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)([OH:11])[CH3:10].C(N(CC)CC)C.[Cl:24][CH2:25][C:26](Cl)=[O:27].Cl>C(OCC)(=O)C.C(OCC)C.C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:26](=[O:27])[CH2:25][Cl:24])=[C:3]([C:9]([OH:11])([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])[CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 688643251-(2-Amino-5-bromo-phenyl)-1-thiophen-2-yl-ethanol

Product 1

HCID 68864161N-[4-Bromo-2-(1-hydroxy-1-thien-2-ylethyl)phenyl]-2-chloroacetamideYield 96.5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-amino-5-bromo-phenyl)-1-thiophen-2-yl-ethanol (3.9 g, 13 mmol) in a mixture of anhydrous THF and diethyl ether (20 mL/20 mL) at 0° C. under nitrogen was added triethyl amine (4 mL, 28.7 mmol) and chloroacetyl chloride (1.6 mL, 20 mmol). After addition, the reaction mixture was slowly warmed to room temperature (rt), stirred for 3 h, and treated with a cold 1N hydrogen chloride aqueous solution (70 mL). Ethyl acetate (100 mL) was added and organic layer separated, dried (Mg2SO4), concentrated to yield the title compound as a white solid (4.7 g, 94%). 1H-NMR (DMSO-d6) δ 10.78 (s, 1H), 8.05 (d, J=8.7 Hz, 1H), 7.51 (dd, J=8.7, 2.2 Hz, 1H), 7.43 (d, J=5.0 Hz, 1H), 7.37 (m, 2H), 6.95 (m, 1H), 6.88 (dd, J=3.4, 0.8 Hz, 1H), 4.26 (d, J=6.9 Hz, 2H), 1.94 (s, 3H).

Workup

  1. additionAfter addition
  2. customorganic layer separated
  3. dry with materialdried (Mg2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b838698a66cb4f4d818d6288fc538cb0
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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