2-Chloroethyl isocyanate → N-(3-carboethoxy-4-phenylthien-2-yl)-N'-(chloroethyl)urea

HRID 1858990Notes

Reaction equation

HRID 1858990 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:18][CH2:19][CH2:20][N:21]=[C:22]=[O:23]>C1(C)C=CC=CC=1>[C:7]([C:6]1[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][S:3][C:2]=1[NH:1][C:22]([NH:21][CH2:20][CH2:19][Cl:18])=[O:23])([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanate2×HCID 73242Ethyl 2-amino-4-phenylthiophene-3-carboxylate

Product 1

HCID 53822359N-(3-carboethoxy-4-phenylthien-2-yl)-N'-(chloroethyl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-amino-3-carboethoxy-4-phenylthiophene, prepared by the method of Gewald Chem. Ber. (1966), 99, 94, (2.47 g, 0.010 mol) in toluene (30 mL) was heated to reflux, treated with 2-chloroethylisocyanate (1.0 mL, 0.012 mol), stirred for 1 hour, treated with a second portion of 2-chloroethylisocyanate (1.0 mL, 0.012 mol), stirred for 1 hour, cooled, and concentrated. The product was crystallized from ethyl acetate/hexane to provide 2.93 g (83%) yield of the title compound.

Workup

  1. temperatureto reflux
  2. stirringstirred for 1 hour
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe product was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-6c36629dae0d4956a37f7d4f15cefbc2
Source dataset
uspto-grants-2000_11
Patent number
US06153614

Reaction notes

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