Phosgene → HCID 178473406, compound

HRID 1419762Notes

Reaction equation

HRID 1419762 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[N:9][N:10]([CH3:22])[C:11]=1[S:12]([NH:15][C:16]([NH:18][CH:19]([CH3:21])[CH3:20])=S)(=[O:14])=[O:13])=[O:5])[CH3:2].C(N(CC)CC)C.C(Cl)(Cl)=O>C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([N:6]1[C:7]2[CH:8]=[N:9][N:10]([CH3:22])[C:11]=2[S:12](=[O:14])(=[O:13])[N:15]=[C:16]1[NH:18][CH:19]([CH3:21])[CH3:20])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 54068939N-(4-Ethoxycarbonylamino-1-methyl-5-pyrazolesulfonyl)-N'-isopropylthiourea

Product 1

HCID 178473406HCID 178473406, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-(4-ethoxycarbonylamino-1-methyl-5-pyrazolesulfonyl)-N'-isopropylthiourea (0.37 g) and triethylamine (0.45 ml) in 5 ml of dry THF at 0° C. was added 1.0 ml of a 20% solution of phosgene in toluene. The mixture was stirred at 0° C. for 30 min. and then evaporated to dryness. The residue was triturated with 10 ml of water, filtered off, rinsed on the filter with water and dried to give 0.27 g (82%) of the title compound; m.p. 141°-145° C.

Workup

  1. customevaporated to dryness
  2. customThe residue was triturated with 10 ml of water
  3. filtrationfiltered off
  4. washrinsed on the
  5. filtrationfilter with water
  6. customdried

Sources & evidence

ORD record
ord-09020a7de5e64f12b1d2d7a6f88471c1
Source dataset
uspto-grants-1999_03
Patent number
US05889002

Reaction notes

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