Phenethyl Isothiocyanate → 1-(4-Chloro-2-(alpha-hydroxybenzyl)benzyl)-3-phenethylthiourea

HRID 442496

Reaction equation

HRID 442496 reaction equation
[NH2:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:4]=1[CH:5]([OH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:18]([N:26]=[C:27]=[S:28])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO.C(N(CC)CC)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:3]([CH2:2][NH:1][C:27]([NH:26][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[S:28])=[C:4]([CH:5]([OH:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:13]=1

Participants

5

Reactant 2

HCID 16741Phenethyl IsothiocyanateHCID 12241006Benzenemethanol,2-(aminomethyl)-5-chloro-a-phenyl-

Product 1

HCID 214154601-(4-Chloro-2-(alpha-hydroxybenzyl)benzyl)-3-phenethylthiourea

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8471TriethylamineSolvent

Procedure

2-aminomethyl-5-chlorobenzhydrol (10 g; 0.04 mole) in 100 ml methanol and 2 ml triethylamine was treated dropwise with a solution of phenethyl isothiocyanate (8.6 g; 0.053 mole) in 25 ml of methanol. After 16 hours at room temperature the reaction mixture was evaporated and the residue was extracted with petroleum ether. The residual oil was recrystallized from diisopropyl ether to yield 1-(4-chloro-2-(α-hydroxybenzyl)benzyl)-3-phenethylthiourea as a white powder (M.Pt. 97° -- 101° ).

Workup

  1. customAfter 16 hours at room temperature the reaction mixture was evaporated
  2. extractionthe residue was extracted with petroleum ether
  3. customThe residual oil was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-93903d4497c1482bb535b4bb2fd9bcc5
Source dataset
uspto-grants-1977_08
Patent number
US04045572

Linked notes

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