Thiophosgene → N,N'-diundecylthiourea

HRID 867449Notes

Reaction equation

HRID 867449 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH2:5]([NH2:16])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:5]([NH:16][C:1]([NH:16][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[S:2])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 11430Potassium CarbonateHCID 81742Undecylamine

Product 1

HCID 14390155N,N'-diundecylthioureaYield 60.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Thiophosgene (10.9 mls, 0.14 moles) is added dropwise to a well stirred mixture of undecylamine (49.9 g, 0.29 moles) and water (400 mls). The mixture is heated to reflux following the addition. After 45 minutes the mixture is allowed to cool while potassium carbonate (20.0 g, 0.14 moles) is added in portions, and is then reheated to reflux. After three hours the mixture is cooled and the product is filtered off, triturated in 2N HCl, refiltered, rinsed with water, and dried. Recrystallization from ethylacetate gave the product (32.7 g) mp 70°-72° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. additionthe addition
  4. additionis added in portions
  5. temperatureto reflux
  6. temperatureAfter three hours the mixture is cooled
  7. filtrationthe product is filtered off
  8. customtriturated in 2N HCl
  9. washrinsed with water
  10. customdried
  11. customRecrystallization from ethylacetate

Sources & evidence

ORD record
ord-29fae9e924ba4186bbab008a06d95d7a
Source dataset
uspto-grants-1988_10
Patent number
US04775677

Reaction notes

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