Ammonia → N-(4-Chlorobenzhydryl)thiourea

HRID 866857

Reaction equation

HRID 866857 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]([N:13]=[C:14]=[S:15])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[NH3:18]>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([NH:13][C:14]([NH2:18])=[S:15])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 218286174-Chlorobenzhydryl isothiocyanate

Product 1

HCID 21312364N-(4-Chlorobenzhydryl)thiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-chlorobenzhydryl isothiocyanate [5.2g (0.02M)] in 50 mls of dry ether at 0° C is treated with NH3 (anhyd.) for 1/2 hour while maintaining a temperature of 0° C with stirring. Stirring is continued an additional 1.5 hours at 9° to 10° C. during which time a white solid appears. The crude thiourea is filtered and washed thoroughly with ether; mp 173°-5° C. The filtrate is concentrated in vacuo to yield additional product. The combined crops of N-(4-chlorobenzhydryl) thiourea are used in the next step without further purification.

Workup

  1. stirringStirring
  2. filtrationThe crude thiourea is filtered
  3. washwashed thoroughly with ether
  4. concentrationThe filtrate is concentrated in vacuo
  5. customto yield additional product
  6. customThe combined crops of N-(4-chlorobenzhydryl) thiourea are used in the next step without further purification

Sources & evidence

ORD record
ord-edd07cff828446d087e0a9b78a66eaf4
Source dataset
uspto-grants-1978_07
Patent number
US04101659

Linked notes

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