Phosgene → 6-chloro-1,1-dioxo-N-propan-2-yl-4H-thieno[3,2-e][1,2,4]thiadiazin-3-amine

HRID 1419743Notes

Reaction equation

HRID 1419743 reaction equation
C(Cl)(Cl)=O.[NH2:5][C:6]1[CH:10]=[C:9]([Cl:11])[S:8][C:7]=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>O1CCCC1>[Cl:11][C:9]1[S:8][C:7]2[S:12](=[O:14])(=[O:13])[N:15]=[C:16]([NH:18][CH:19]([CH3:21])[CH3:20])[NH:5][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 11066983N-(3-Amino-5-chloro-2-thienylsulfonyl)-N'-isopropylthiourea

Product 1

HCID 1784569956-chloro-1,1-dioxo-N-propan-2-yl-4H-thieno[3,2-e][1,2,4]thiadiazin-3-amineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Phosgene (1.14 ml, 20% in toluene) was added dropwise to a solution of N-(3-amino-5-chloro-2-thienylsulfonyl)-N'-isopropylthiourea (0.63 g, 2.0 mmol) and dry triethylamine (0.56 ml, 4.0 mmol) in dry tetrahydrofuran (10 ml) with stirring at 0° C. The mixture was stirred for 1 h at 0° C., and evaporated to dryness. The residue was triturated with water, and the precipitate was isolated by filtration, washed with water and dried affording 0.52 g (93%) of the title compound.

Workup

  1. stirringThe mixture was stirred for 1 h at 0° C.
  2. customevaporated to dryness
  3. customThe residue was triturated with water
  4. customthe precipitate was isolated by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-7192937a7ec64d59920ed02bc42be808
Source dataset
uspto-grants-1999_03
Patent number
US05889002

Reaction notes

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