N-(1-Hydroxy-2-methylpropan-2-yl)thiourea → 4-Bromo-5-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}thiophene-2-carbonitrile hydrochloride

HRID 1436388Notes

Reaction equation

HRID 1436388 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]#[N:12])[S:5][C:6]=1[C:7](=O)[CH2:8][Cl:9].[OH:13][CH2:14][C:15]([NH:18][C:19]([NH2:21])=[S:20])([CH3:17])[CH3:16]>C(O)C>[ClH:9].[Br:1][C:2]1[CH:3]=[C:4]([C:11]#[N:12])[S:5][C:6]=1[C:7]1[N:21]=[C:19]([NH:18][C:15]([CH3:17])([CH3:16])[CH2:14][OH:13])[S:20][CH:8]=1

Participants

4

Reactant 2

HCID 22768414N-(1-Hydroxy-2-methylpropan-2-yl)thioureaHCID 866185894-Bromo-5-(chloroacetyl)thiophene-2-carbonitrile

Product 1

HCID 866185904-Bromo-5-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}thiophene-2-carbonitrile hydrochlorideYield 58.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-bromo-5-(chloroacetyl)thiophene-2-carbonitrile (430 mg, 1.6 mmol), prepared in the previous step, and N-(2-hydroxy-1,1-dimethylethyl)thiourea (241.2 mg, 1.6 mmol), prepared in step 2 of Example 52, in 10 mL of absolute ethanol was refluxed under nitrogen for 2.5 h. The solvent was concentrated to approximately two thirds its volume. The solid present was collected by filtration and dried under reduced pressure to give 4-bromo-5-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}thiophene-2-carbonitrile hydrochloride (367.8 mg, 58%) as a yellow solid, mp 177.5-178.5° C.; MS (ESI) m/z 358 [M+H]+.

Workup

  1. temperaturewas refluxed under nitrogen for 2.5 h
  2. concentrationThe solvent was concentrated to approximately two thirds its volume
  3. filtrationThe solid present was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-eca068fe91ac496db3a5a10a3fc2ca45
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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