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tert-Butanol → 3-(4-Chloro-phenyl)-isothiazole-4-carboxylic acid tert-butyl ester

HRID 388418
Notes
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Reaction equation

HRID 388418 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][S:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:16][C:17](O)([CH3:19])[CH3:18].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:17]([O:14][C:13]([C:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:9][S:10][CH:11]=1)=[O:15])([CH3:19])([CH3:18])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 12437453HCID 12437453, compound

Product 1

HCID 584329863-(4-Chloro-phenyl)-isothiazole-4-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a mixture of 7 (3.35 g), DMAP (1.7 g) and tBuOH (5.2 g) in CH2Cl2 (50 ml) is added 3.2 g of EDCI and the clear solution is stirred over the weekend. Additional CH2Cl2 (100 ml) is added and the mixture is washed with 1N HCl (2×150 ml), sat. NaHCO3 (150 ml), brine (150 ml), dried and concentrated. This afforded 3.75 g of 8 as a pale yellow oil.

Workup

  1. washthe mixture is washed with 1N HCl (2×150 ml), sat. NaHCO3 (150 ml), brine (150 ml)
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-67fd5616b4144d0ca26758dc4ccd024f
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08377953B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes