Ethanol → HCID 57967274, compound

HRID 1475574Notes

Reaction equation

HRID 1475574 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]=[C:12]=[S:13])=[O:10])=[CH:4][CH:3]=1.CCO.[O:17]1[CH2:22][CH2:21][CH2:20][O:19][CH:18]1[C:23]1[CH:24]=[CH:25][C:26]([C:29]2[S:37][C:36]3[C:31](=[N:32][CH:33]=[CH:34][C:35]=3[O:38][C:39]3[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][C:40]=3[F:46])[CH:30]=2)=[N:27][CH:28]=1>C1(C)C=CC=CC=1>[O:17]1[CH2:22][CH2:21][CH2:20][O:19][CH:18]1[C:23]1[CH:24]=[CH:25][C:26]([C:29]2[S:37][C:36]3[C:31](=[N:32][CH:33]=[CH:34][C:35]=3[O:38][C:39]3[CH:45]=[CH:44][C:42]([NH:43][C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[S:13])=[CH:41][C:40]=3[F:46])[CH:30]=2)=[N:27][CH:28]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 231532482-(4-Fluorophenyl)acetyl isothiocyanateHCID 579672584-(2-(5-(1,3-Dioxan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline

Product 1

HCID 57967274HCID 57967274, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of isothiocyanate 2 (13.17 g, 67.4 mmol) in a mixture of toluene (100 ml)/EtOH (100 ml) in a 500 mL round-bottom flask was added aniline 31 (23.8 g, 56.2 mmol). The mixture was stirred for 1 h at room temperature and concentrated. The solid was triturated with toluene (100 mL) for 1 h, collected by filtration, washed with toluene (20 ml). The solid was dried under vacuum for 2 h to give crude 32 (35.10 g) which was used in the next step without any further purification. MS (m/z): 619.1 (M+1)

Workup

  1. concentrationconcentrated
  2. customThe solid was triturated with toluene (100 mL) for 1 h
  3. filtrationcollected by filtration
  4. washwashed with toluene (20 ml)
  5. customThe solid was dried under vacuum for 2 h

Sources & evidence

ORD record
ord-7cd1eb4454a24c51ae5d904fa51c25d5
Source dataset
uspto-grants-2015_04
Patent number
US09018378B2

Reaction notes

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