4-Methyloxybenzyl chloride → (4-Methoxyphenyl)methyl carbamimidothioate--hydrogen chloride (1/1)

HRID 1788689Notes

Reaction equation

HRID 1788689 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[CH3:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][Cl:12])=[CH:9][CH:8]=1>O1CCCC1.CCOCC>[ClH:12].[CH3:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][S:3][C:2](=[NH:4])[NH2:1])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 2723790Thiourea

Product 1

HCID 13885856(4-Methoxyphenyl)methyl carbamimidothioate--hydrogen chloride (1/1)Yield 93.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of thiourea (38 g, 50.0 mmole) in dry tetrahydrofuran (40 ml) was cooled to 0° C. under argon and was treated dropwise with 4-methoxybenzylchloride (8.0 g, 50.0 mmole). After the addition was completed, the cooling bath was removed and the reaction was allowed to stir at room temperature for 2 hours. It was then heated at 60-65° C. for 4 hours whereupon a colorless voluminous precipitate was formed. The reaction was allowed to cool down to room temperature and was, diluted with anhydrous ether. The solid was filtered off and washed with anhydrous ether to give 10.92 g of 2-(4-methoxybenzyl)-2-thiopseudourea, hydrochloride, melting point 161-163.5° C. Analysis Calc'd. for C9H12N2OS.HCl: C, 46.45; H, 5.63; N, 12.04; S, 13.78; Cl, 15.23. Found: C, 46.48; H, 5.64; N, 12.25; S, 13.74; Cl, 15.31.

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. temperatureIt was then heated at 60-65° C. for 4 hours whereupon a colorless voluminous precipitate
  4. customwas formed
  5. temperatureto cool down to room temperature
  6. filtrationThe solid was filtered off
  7. washwashed with anhydrous ether

Sources & evidence

ORD record
ord-7608171c4948438485513da06239373e
Source dataset
uspto-grants-1987_08
Patent number
US04684656

Reaction notes

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