Hexane → HCID 11719232, compound

HRID 1713048Notes

Reaction equation

HRID 1713048 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:17]=[C:16]([C:18](OCC)=[O:19])[NH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:23]([CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:24]=[S:25].C(N(CC)CC)C.CCCCCC>[N-]=C=S.C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][N:23]1[C:24](=[S:25])[N:15]2[C:13]3[N:14]=[C:10]([C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=4)[S:11][C:12]=3[CH:17]=[C:16]2[C:18]1=[O:19])[CH3:33]

Participants

8

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 123372Ethyl 4-isothiocyanatobutanoateHCID 59463473HCID 59463473, compound

Product 1

HCID 11719232HCID 11719232, compound

Reagents, catalysts & solvents 3

HCID 178418790HCID 178418790, compoundCatalystHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

As depicted in Scheme 27 below, ethyl 2-(4-nitrophenyl)-4H-pyrrolo[2,3-d]thiazole-5-carboxylate (0.1 mmol) is placed in a heavy-walled glass tube equipped with a threaded Teflon plug, and ethyl 4-isothiocyanatobutyrate (1.03 mmol, 10 molequivalents) and triethylamine (2 mmol, 20 molequivalents) are added thereto. The glass tube is sealed and the reaction mixture is heated at 130° C. while stirring overnight (18 hours). Additional isothiocyanate (10 drops, 10 molequivalents) is added thereafter and heating is continued while stirring at 130° C. for 6 additional hours. The mixture is then dissolved in chloroform and the purified final product is isolated by column chromatography on silica, using a 9:1 hexane:ethyl acetate mixture as eluent.

Workup

  1. customis placed in a heavy-walled glass tube
  2. additionare added
  3. customThe glass tube is sealed
  4. temperatureheating
  5. stirringwhile stirring at 130° C. for 6 additional hours
  6. customthe purified final product
  7. customis isolated by column chromatography on silica

Sources & evidence

ORD record
ord-d8d5e4437fac4778b09023ec7ef29b39
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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