Phosgene → HCID 178473407, compound

HRID 1975912Notes

Reaction equation

HRID 1975912 reaction equation
[C:1]([C:3]1[C:4]([S:15]([NH:18][C:19]([NH:21][CH:22]([CH3:24])[CH3:23])=S)(=[O:17])=[O:16])=[C:5]([NH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:6][C:7]=1[CH3:8])#[N:2].C(N(CC)CC)C.C(Cl)(Cl)=O>C1COCC1.C1(C)C=CC=CC=1>[C:1]([C:3]1[C:4]2[S:15](=[O:17])(=[O:16])[N:18]=[C:19]([NH:21][CH:22]([CH3:24])[CH3:23])[N:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]=2[S:6][C:7]=1[CH3:8])#[N:2]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 21999987HCID 21999987, compound

Product 1

HCID 178473407HCID 178473407, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-(4-cyano-2-ethoxycarbonylamino-5-methyl-3-thienylsulfonyl)-N′-isopropylthiourea (0.3 g) and triethylamine (320 μl) in 10 ml of dry THF at 0° C. was added 750 μl of a 20% solution of phosgene in toluene. The mixture was stirred at 0° C. for 1 h 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 0.24 g of crude title compound; m.p. 116-119° C. The product was used for the next step without purification.

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-0ecb6ad7ab3f476692915fff8e6d3af5
Source dataset
uspto-grants-2001_05
Patent number
US06225310B1

Reaction notes

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