Phosgene → HCID 178456980, compound

HRID 1066091Notes

Reaction equation

HRID 1066091 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]([NH:18][CH:19]([CH3:21])[CH3:20])=S)(=[O:14])=[O:13].C(N(CC)CC)C.C(Cl)(Cl)=O>C1COCC1.C1(C)C=CC=CC=1>[CH:19]([NH:18][C:16]1[NH:1][C:2]2[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=2[S:12](=[O:14])(=[O:13])[N:15]=1)([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 21197764HCID 21197764, compound

Product 1

HCID 178456980HCID 178456980, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of N-(2-amino-4-(methanesulfonyl)benzenesulfonyl)-N′-isopropylthiourea (3.0 g) and triethylamine (1.7 g) in 30 ml of dry THF at 0° C. was added 5.2 ml of a 20% solution of phosgene in toluene during 5 min. The mixture was stirred at 0° C. for 1 h and then evaporated in vacuo. The white, solid residue was triturated with 50 ml of water for 45 min. and then the product was isolated by filtration. The filter cake was rinsed on the filter with water and dried to give the title compound as white crystals; m.p. >300° C.

Workup

  1. customevaporated in vacuo
  2. customThe white, solid residue was triturated with 50 ml of water for 45 min.
  3. customthe product was isolated by filtration
  4. washThe filter cake was rinsed on the
  5. filtrationfilter with water
  6. customdried

Sources & evidence

ORD record
ord-50d6ebae865a451f84f4937385203683
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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