Ammonia → HCID 178513943, compound

HRID 1984920Notes

Reaction equation

HRID 1984920 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19](O)=[O:20])[CH2:15][CH2:14]2)(=[O:10])=[O:9])=[C:4]([O:22][C:23]([F:26])([F:25])[F:24])[CH:3]=1.C([N:29](CC)CC)C.ClC(OCC)=O.N>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]([NH2:29])=[O:20])[CH2:15][CH2:14]2)(=[O:10])=[O:9])=[C:4]([O:22][C:23]([F:26])([F:25])[F:24])[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178525720HCID 178525720, compound

Product 1

HCID 178513943HCID 178513943, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of trans-4-[(4-bromo-2-trifluoromethoxy-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid (7.14 g, 15.5 mmol) and triethylamine (2.35 mL, 16.9 mmol) in THF (25 mL) was cooled to 0° C. To the mixture was added ethyl chloroformate (1.62 mL, 17 mmol) in THF (5 mL) over 10 min. After stirring at 0° C. for 15 min, aqueous ammonia (27 mL) was added dropwise and the mixture was stirred at ambient temperature for 2 hr. The mixture was concentrated under reduced pressure and the concentrate was treated with water to give a solid. The solid was filtered and washed with water and hexanes to give trans-4-[(4-bromo-2-trifluoromethoxy-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid amide as a white solid (4.2 g, 59%).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 2 hr
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionthe concentrate was treated with water
  4. customto give a solid
  5. filtrationThe solid was filtered
  6. washwashed with water and hexanes

Sources & evidence

ORD record
ord-d62e019609654c6a9df1fb9034d1d2cf
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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