Methyl Isocyanate → HCID 15037502, compound

HRID 704737Notes

Reaction equation

HRID 704737 reaction equation
[N:1]([CH3:4])=[C:2]=[O:3].[NH2:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[N:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:17]3[CH:27]=[CH:28][CH:29]=[CH:30][C:16]=3[N:15]=2)[CH2:9]1.[Cl-].[Cl-].[Ca+2]>O1CCCC1>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:18]2[C:17]3[CH:27]=[CH:28][CH:29]=[CH:30][C:16]=3[N:15]=[C:14]2[NH:13][CH:10]2[CH2:11][CH2:12][N:8]([CH2:7][CH2:6][NH:5][C:2]([NH:1][CH3:4])=[O:3])[CH2:9]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 12228Methyl Isocyanate2×HCID 5284359Calcium ChlorideHCID 15037482HCID 15037482, compound

Product 1

HCID 15037502HCID 15037502, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.9 parts of isocyanatomethane, 5.3 parts of N-[1-(2-amino-ethyl)-3-pyrrolidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine and 63 parts of tetrahydrofuran was stirred for 1.5 hour at room temperature using a CaCl2 -tube. Another portion of 0.9 parts of isocyanatomethane was added and stirring was continued for 1.5 hour at room temperature. The precipitated product was filtered off, washed with tetrahydrofuran and dried in vacuo at room temperature, yielding 5.0 parts (81%) of N-[2-[3-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-pyrrolidinyl]ethyl]-N'-methylurea; mp. 161.1° C. (compound 188).

Workup

  1. stirringstirring
  2. waitwas continued for 1.5 hour at room temperature
  3. filtrationThe precipitated product was filtered off
  4. washwashed with tetrahydrofuran
  5. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-038c8b35b40847b293be2f30b74fde1f
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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