Acetyl chloride → HCID 21483029, compound

HRID 1415628Notes

Reaction equation

HRID 1415628 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]([NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH3:22])=[CH:15][C:14]=1[NH2:23])=[S:11])=[O:8]>C1(C)C=CC=CC=1>[CH3:5][O:6][C:7]([NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH3:22])=[CH:15][C:14]=1[NH:23][C:1](=[O:3])[CH3:2])=[S:11])=[O:8]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 21441048HCID 21441048, compound

Product 1

HCID 21483029HCID 21483029, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Acetyl chloride (4.53 g.; 0.058 mole) was added to a suspension of 1-methoxycarbonyl-3-(2-amino-4-n-butylphenyl)-thiourea (16.0 g; 0.057 mol3) in dry toluene (230 ml) and the stirred mixture was refluxed for ninety minutes. During this time the solid gradually dissolved to give a slightly turbid solution. On cooling to laboratory temperature a solid separated which was filtered off and recrystallised to give 1-methoxycarbonyl-3-(2-acetamido-4-n-butylphenyl)thiourea (11.4 g), m.p. 173°-174° C. (with decomposition).

Workup

  1. temperaturethe stirred mixture was refluxed for ninety minutes
  2. dissolutionDuring this time the solid gradually dissolved
  3. customto give a slightly turbid solution
  4. temperatureOn cooling to laboratory temperature a solid
  5. customseparated which
  6. filtrationwas filtered off
  7. customrecrystallised

Sources & evidence

ORD record
ord-01ce4fb12a8547218878a587be298a18
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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