Phosgene → HCID 20300366, compound

HRID 1076199Notes

Reaction equation

HRID 1076199 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]=1[C:11]#[N:12].[CH2:17]([NH:19][CH2:20]C)C.C(N(CC)CC)C>C1C=CC=CC=1>[C:11]([C:10]1[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][S:7][C:6]=1[NH:5][C:1]([N:19]([CH3:20])[CH3:17])=[O:2])#[N:12]

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 8021DiethylamineHCID 8471TriethylamineHCID 5968662-Amino-4-(1,1-dimethylethyl)-3-thiophenecarbonitrile

Product 1

HCID 20300366HCID 20300366, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 3.04 g phosgene in about 25 ml benzene was added to a cooled (0°C.) solution of 5 g 2-amino-3-cyano-4-t-butylthiophene, 5 g diethylamine and 8.4 g triethylamine in 100 ml benzene. The reaction mixture was warmed to about 25°C. and maintained at this temperature for about 16 hours. The reaction mixture was filtered and the filtrate was evaporated to give a black oil. The oil was chromatographed on silica gel. The product, a brown solid melting at 120°-125°C., was eluted from the silica gel with 1:1 ether-hexane. The infrared spectrum of the product showed strong cyano absorption at 4.6 microns and strong carbonyl absorption at 6.0 microns. Sulfur analysis for the product is tabulated in Table I.

Workup

  1. temperaturemaintained at this temperature for about 16 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. customto give a black oil
  5. customThe oil was chromatographed on silica gel
  6. washThe product, a brown solid melting at 120°-125°C., was eluted from the silica gel with 1:1 ether-hexane
  7. customcyano absorption
  8. customat 4.6 microns and strong carbonyl absorption at 6.0 microns

Sources & evidence

ORD record
ord-05d35ecd3125483f807dfaf84c3db4ef
Source dataset
uspto-grants-1976_05
Patent number
US03956315

Reaction notes

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