Phosgene → HCID 178446297, compound

HRID 1975916Notes

Reaction equation

HRID 1975916 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][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=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][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[NH:5][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 10991483HCID 10991483, compound

Product 1

HCID 178446297HCID 178446297, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Phosgene (0.242 ml, 20% in toluene) was added dropwise to a solution of N-(3-amino-5-chloro-2-thienylsulfonyl)-N′-(3-methylbutyl)thiourea (0.153 g, 0.42 mmol) and dry triethylamine (0.118 ml, 0.85 mmol) in dry tetrahydrofuran (3 ml) with stirring at 0° C. The mixture was stirred for 2 h at 0° C., and evaporated to dryness. Crystallisation was obtained from ethyl acetate, and the precipitate was isolated by filtration, washed with water and dried affording 38 mg (27%) of the title compound. mp 230-231.5° C., 1H-NMR (DMSO-d6): δ0.90 (d, 6H, 2×CH3), 1.40 (q, 2H, CH2),1.60 (m, 1H, CH), 3.20 (q, 2H, CH2), 7.05 (s, 1H, H-5), 7.25 (br s, 1H, NH), 10.95 (s, 1H, NH). MS: M/e 307(M+).

Workup

  1. stirringThe mixture was stirred for 2 h at 0° C.
  2. customevaporated to dryness
  3. customCrystallisation
  4. customwas obtained from ethyl acetate
  5. customthe precipitate was isolated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-78770fc323f74a3eab3720891fcea4c0
Source dataset
uspto-grants-2001_05
Patent number
US06225310B1

Reaction notes

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