3-Chloroaniline → HCID 68408190, compound

HRID 2244407Notes

Reaction equation

HRID 2244407 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([CH3:17])=[CH:12][C:13]=1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C)C=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:10][C:11]([CH3:17])=[CH:12][C:13]=1[C:14](=[O:16])[NH:22][C:21]1[CH:23]=[CH:24][CH:25]=[C:19]([Cl:18])[CH:20]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 79323-ChloroanilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 63615646HCID 63615646, compound

Product 1

HCID 68408190HCID 68408190, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-tert-butoxycarbonylamino-5-methyl-thiophene-3-carboxylic acid (1.16 g, 4.49 mmol) in dimethylformamide (50.00 ml) was treated with 3-chloro aniline (0.86 g, 6.73 mmol), DIPEA (1.74 g, 13.47 mmol) and TBTU (2.16 g, 6.73 mmol) and stirred at room temperature for 48 h. The volatiles were evaporated and the residue purified by flash chromatography (heptane/ethyl acetate), to yield [3-(3-chloro-phenylcarbamoyl)-5-methyl-thiophen-2-yl]-carbamic acid tert-butyl ester (0.45 g, 27%) as a yellow solid, MS (ISP): m/e=368.6 (M+H+)

Workup

  1. customThe volatiles were evaporated
  2. customthe residue purified by flash chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-e699837cf8b34c9ba1533eeb2cbeeac0
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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