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

HRID 1436389Notes

Reaction equation

HRID 1436389 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([C:10]#[N:11])[S:8][CH:9]=1)=O.[OH:12][CH2:13][C:14]([NH:17][C:18]([NH2:20])=[S:19])([CH3:16])[CH3:15]>C(O)C>[ClH:1].[OH:12][CH2:13][C:14]([NH:17][C:18]1[S:19][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]([C:10]#[N:11])[S:8][CH:9]=2)[N:20]=1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 22768414N-(1-Hydroxy-2-methylpropan-2-yl)thioureaHCID 866185944-(Chloroacetyl)thiophene-2-carbonitrile

Product 1

HCID 866185924-{2-[(2-Hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}thiophene-2-carbonitrile hydrochlorideYield 86.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(chloroacetyl)thiophene-2-carbonitrile (500.5 mg, 2.73 mmol), prepared in step 1 of Example 59, and N-(2-hydroxy-1,1-dimethylethyl)thiourea (399.4 mg, 2.69 mmol), prepared in step 2 of Example 52, in 20 mL of ethanol was stirred under nitrogen at room temperature overnight. The solid was collected by filtration and dried under reduced pressure to give 4-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}thiophene-2-carbonitrile hydrochloride (738.1 mg, 86%) as a light tan solid, mp 197-201° C.; MS (ES) m/z 277.9 [M−H]−.

Workup

  1. filtrationThe solid was collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-d47c5eb13c4248d88b33eb6affb95f06
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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