Thiophosgene → Thiourea, N,N'-didodecyl-

HRID 867450Notes

Reaction equation

HRID 867450 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH2:5]([NH2:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C1(C)C=CC=CC=1>[CH2:5]([NH:17][C:1]([NH:17][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[S:2])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 13583Dodecylamine

Product 1

HCID 3034200Thiourea, N,N'-didodecyl-Yield 75.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thiophosgene (10.0 mls, 0.13 moles) is added dropwise to a stirred solution of dodecylamine (100 g, 0.54 moles) in toluene (210 mls). The mixture is heated to reflux for four hours then cooled in an icebath. The precipitate is filtered off, rinsed with toluene then ether, and dried, then treated with hot dilute HCl, rinsed with water and redried. Recrystallization from ethyl acetate gave the product (40.5 g), mp 75°-78° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for four hours
  3. temperaturethen cooled in an icebath
  4. filtrationThe precipitate is filtered off
  5. washrinsed with toluene
  6. dry with materialether, and dried
  7. additiontreated with hot dilute HCl
  8. washrinsed with water
  9. customredried
  10. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-29fb0190e84f49ad91a2acf43365348d
Source dataset
uspto-grants-1988_10
Patent number
US04775677

Reaction notes

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