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Hexane → HCID 25029879, compound

HRID 1436419
Notes
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Reaction equation

HRID 1436419 reaction equation
C(N(CC)C(C)C)(C)C.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([NH:24][C:25]([CH3:29])([CH3:28])[CH2:26][OH:27])[S:22][CH:23]=2)=[CH:15][CH:14]=1)([O-:12])=[O:11].Cl[C:31](Cl)([O:33]C(=O)OC(Cl)(Cl)Cl)Cl.CCCCCC>C(Cl)Cl.C(OCC)(=O)C>[CH3:28][C:25]1([CH3:29])[CH2:26][O:27][C:31](=[O:33])[N:24]1[C:21]1[S:22][CH:23]=[C:19]([C:16]2[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:18][CH:17]=2)[N:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 866186072-{[4-(4-Nitrophenyl)-1,3-thiazol-2-yl]amino}-2-methylpropan-1-ol

Product 1

HCID 25029879HCID 25029879, compoundYield 117.4%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
2×
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

N,N-diisopropylethylamine (1.0 mL, 5.7 mmol) was added dropwise to a solution of 2-{[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino}-2-methylpropan-1-ol (0.7 g, 2.4 mmol), prepared in the previous step, in 20 mL of dry methylene chloride at 0° C., followed by triphosgene (0.8 g, 2.8 mmol) in 20 mL of dry dichloromethane. The orange solution was stirred at 0° C. for 3 h, and then allowed to warm to room temperature. TLC (3:1 hexane:ethyl acetate) indicated the reaction was complete. The reaction was washed with 2N HCl and the aqueous layer was extracted with methylene chloride. The combined organic layer was dried (anhydrous MgSO4), filtered and concentrated under reduced pressure to give 900 mg of a yellow solid. Purification of the solid on silica gel using a stepwise gradient of 6:1 to 5:1 hexane:ethyl acetate gave the title compound (268 mg, 35%), mp 176-179° C.

Workup

  1. temperatureto warm to room temperature
  2. washThe reaction was washed with 2N HCl
  3. extractionthe aqueous layer was extracted with methylene chloride
  4. dry with materialThe combined organic layer was dried (anhydrous MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e5c50a76b1646cabc3818bb49bc3c48
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07618990B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes