Triethylamine → Acetamide, 2-bromo-N-[2-[(triphenylmethyl)thio]ethyl]-

HRID 1417914Notes

Reaction equation

HRID 1417914 reaction equation
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:8][CH2:9][CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[Br:31][CH2:32][C:33](Br)=[O:34]>C(Cl)Cl>[Br:31][CH2:32][C:33]([NH:11][CH2:10][CH2:9][S:8][C:7]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 262764S-Tritylcysteamine

Product 1

HCID 11259232Acetamide, 2-bromo-N-[2-[(triphenylmethyl)thio]ethyl]-Yield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution S-triphenylmethyl-2-aminoethanethiol (48 g, 0.15 mol) and Et3N (20.9 ml, 0.15 mol) in DCM (180 ml) was slowly added to a stirred solution of bromoacetyl bromide (13.9 ml, 0.15 mol) in DCM (100 ml) at a temperature of -20° C. The reaction was allowed to warm to room temperature over a one hour period. The reaction was washed with 500 ml portions of H2O, 0.2N HCl, saturated NaHCO3, and saturated NaCl. The organic solution was dried (MgSO4) and concentrated to an oil. This oil was crystallized from DCM-hexane to give product (54.9 g, 83%) as a colorless solid, MP 137°-139.5° C. (J. A. Wolff, Ph.D. Thesis, Massachusetts Institute of Technology, February 1992, MP 130°-135° C.

Workup

  1. washThe reaction was washed with 500 ml portions of H2O, 0.2N HCl, saturated NaHCO3, and saturated NaCl
  2. dry with materialThe organic solution was dried (MgSO4)
  3. concentrationconcentrated to an oil
  4. customThis oil was crystallized from DCM-hexane

Sources & evidence

ORD record
ord-b021febcd2f14856a654b4ae006222c1
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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